Target Binding Site Detail

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Target General Information
Ligand General Information
Drug Binding Sites of Target
References
Target General Information  Top
Target ID T80423 Target Info
Target Name von Hippel-Lindau disease tumor suppressor (VHL)
Synonyms pVHL; Protein G7
Target Type Patented-recorded Target
Gene Name VHL
UniProt ID
VHL_HUMAN
Ligand General Information  Top
Ligand Name S-(Dimethylarsenic)Cysteine Ligand Info
Canonical SMILES C[As](C)SCC(C(=O)O)N
InChI 1S/C5H12AsNO2S/c1-6(2)10-3-4(7)5(8)9/h4H,3,7H2,1-2H3,(H,8,9)/t4-/m0/s1
InChIKey UKLXSOVDMSQHMM-BYPYZUCNSA-N
PubChem Compound ID 17753880
Drug Binding Sites of Target  Top
PDB ID: 4B9K      pVHL-ELOB-ELOC complex_(2S,4R)-1-(3-amino-2-methylbenzoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide bound
Method X-ray diffraction Resolution 2.00 Å Mutation No [1]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNQ
145
PIFANITLPV
155
YTLKERCLQV
165

VRSLVKPENY
175
RRLDIVRSLY
185
EDLEDHPNVQ
195
KDLERLT
Residue
Distance (Å)
ILE75
3.475
PHE76
1.330
ASN78
1.324
ARG79
3.242
LEU101
4.958
GLY104
3.424
Residue
Distance (Å)
THR105
3.378
GLY106
3.643
PHE148
3.323
ALA149
2.840
ASN150
3.836
ILE151
2.876
PDB ID: 4AWJ      pVHL:EloB:EloC complex, in complex with capped Hydroxyproline
Method X-ray diffraction Resolution 2.50 Å Mutation No [2]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
PIFANITLPV
155
YTLKERCLQV
165

VRSLVKPENY
175
RRLDIVRSLY
185
EDLEDHPNVQ
195
KDLER
Residue
Distance (Å)
ILE75
3.462
PHE76
1.329
ASN78
1.329
ARG79
3.175
LEU101
4.801
GLY104
3.258
Residue
Distance (Å)
THR105
3.293
GLY106
4.162
PHE148
3.449
ALA149
3.219
ASN150
3.860
ILE151
2.850
PDB ID: 6GMN      pVHL:EloB:EloC in complex with methyl 4H-furo[3,2-b]pyrrole-5-carboxylate
Method X-ray diffraction Resolution 1.94 Å Mutation No [3]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
PIFANITLPV
155
YTLKERCLQV
165

VRSLVKPENY
175
RRLDIVRSLY
185
EDLEDHPNVQ
195
KDLERL
Residue
Distance (Å)
ILE75
3.581
PHE76
1.325
ASN78
1.332
ARG79
3.138
LEU101
4.814
GLY104
3.179
Residue
Distance (Å)
THR105
3.753
GLY106
3.494
PHE148
3.508
ALA149
2.900
ASN150
3.728
ILE151
2.756
PDB ID: 4W9F      pVHL:EloB:EloC in complex with (2S,4R)-1-(3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 5)
Method X-ray diffraction Resolution 2.10 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLND
143
GQPIFANITL
153
PVYTLKERCL
163

QVVRSLVKPE
173
NYRRLDIVRS
183
LYEDLEDHPN
193
VQKDLERLTQ
203
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:157 or .C:158 or .C:159 or .C:160 or .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
THR157
3.236
LEU158
2.389
LYS159
2.793
GLU160
4.765
ILE75
3.433
PHE76
1.329
ASN78
1.331
ARG79
3.252
Residue
Distance (Å)
LEU101
4.904
GLY104
3.306
THR105
3.189
GLY106
3.477
PHE148
3.626
ALA149
2.939
ASN150
3.789
ILE151
2.862
PDB ID: 4W9H      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-acetamido-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 7)
Method X-ray diffraction Resolution 2.10 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:157 or .C:158 or .C:159 or .C:160 or .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
THR157
3.324
LEU158
2.621
LYS159
2.596
GLU160
4.829
ILE75
3.476
PHE76
1.336
ASN78
1.328
ARG79
3.291
Residue
Distance (Å)
LEU101
4.895
GLY104
3.162
THR105
3.246
GLY106
3.493
PHE148
3.475
ALA149
3.019
ASN150
3.838
ILE151
2.884
PDB ID: 4W9K      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-((S)-2-acetamido-3-phenylpropanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 14)
Method X-ray diffraction Resolution 2.10 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.425
PHE76
1.341
ASN78
1.329
ARG79
3.157
GLY104
3.004
THR105
3.140
Residue
Distance (Å)
GLY106
3.669
PHE148
3.507
ALA149
2.911
ASN150
3.634
ILE151
2.904
PDB ID: 5NVV      pVHL:EloB:EloC in complex with (2S,4R)-4-hydroxy-1-((S)-2-(2-hydroxyacetamido)-3,3-dimethylbutanoyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 3)
Method X-ray diffraction Resolution 2.10 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.460
PHE76
1.336
ASN78
1.331
ARG79
3.191
LEU101
4.959
GLY104
3.074
Residue
Distance (Å)
THR105
3.256
GLY106
3.654
PHE148
3.488
ALA149
2.995
ASN150
3.671
ILE151
2.807
PDB ID: 5NW1      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-(cyclobutanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 18)
Method X-ray diffraction Resolution 2.10 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.472
PHE76
1.341
ASN78
1.331
ARG79
3.259
GLY104
3.051
THR105
3.258
Residue
Distance (Å)
GLY106
3.616
PHE148
3.783
ALA149
2.957
ASN150
3.636
ILE151
2.866
PDB ID: 4BKS      von Hippel Lindau protein:ElonginB:ElonginC complex, in complex with (2S,4R)-1-ethanoyl-N-[[4-(1,3-oxazol-5-yl)phenyl]methyl]-4-oxidanyl-pyrrolidine-2-carboxamide
Method X-ray diffraction Resolution 2.20 Å Mutation No [6]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNQ
145
PIFANITLPV
155
YTLKERCLQV
165

VRSLVKPENY
175
RRLDIVRSLY
185
EDLEDHPNVQ
195
KDLERLT
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.316
PHE76
1.344
ASN78
1.332
ARG79
3.108
LEU101
4.855
GLY104
2.947
Residue
Distance (Å)
THR105
3.141
GLY106
3.927
PHE148
3.332
ALA149
2.789
ASN150
3.758
ILE151
2.807
PDB ID: 4W9C      pVHL:EloB:EloC in complex with (2S,4R)-1-(3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(oxazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 2)
Method X-ray diffraction Resolution 2.20 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.549
PHE76
1.335
ASN78
1.334
ARG79
3.224
LEU101
4.807
GLY104
3.148
Residue
Distance (Å)
THR105
3.211
GLY106
3.539
PHE148
3.722
ALA149
2.879
ASN150
3.812
ILE151
2.834
PDB ID: 4W9D      pVHL:EloB:EloC in complex with (2S,4R)-1-(3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methyloxazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 3)
Method X-ray diffraction Resolution 2.20 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.532
PHE76
1.336
ASN78
1.328
ARG79
3.311
LEU101
4.734
GLY104
3.088
Residue
Distance (Å)
THR105
3.257
GLY106
3.486
PHE148
3.430
ALA149
2.978
ASN150
3.799
ILE151
2.850
PDB ID: 4W9J      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-((S)-2-acetamido-4-methylpentanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 13)
Method X-ray diffraction Resolution 2.20 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.399
PHE76
1.330
ASN78
1.333
ARG79
3.256
GLY104
3.135
THR105
3.358
Residue
Distance (Å)
GLY106
3.688
PHE148
3.432
ALA149
2.955
ASN150
3.644
ILE151
2.805
PDB ID: 4W9L      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-((S)-2-acetamido-3,3-dimethylbutanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 15)
Method X-ray diffraction Resolution 2.20 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.496
PHE76
1.331
ASN78
1.335
ARG79
3.226
GLY104
3.139
THR105
3.282
Residue
Distance (Å)
GLY106
3.591
PHE148
3.494
ALA149
2.916
ASN150
3.733
ILE151
2.889
PDB ID: 5NVW      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-(cyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 6)
Method X-ray diffraction Resolution 2.20 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.389
PHE76
1.335
ASN78
1.329
ARG79
3.260
GLY104
2.983
THR105
3.271
Residue
Distance (Å)
GLY106
3.500
PHE148
3.385
ALA149
2.941
ASN150
3.701
ILE151
2.771
PDB ID: 5NVX      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-(1-fluorocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 10)
Method X-ray diffraction Resolution 2.20 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.485
PHE76
1.336
ASN78
1.333
ARG79
3.234
LEU101
4.934
GLY104
2.964
Residue
Distance (Å)
THR105
3.305
GLY106
3.682
PHE148
3.449
ALA149
2.934
ASN150
3.699
ILE151
2.759
PDB ID: 5NW2      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-3,3-dimethyl-2-(oxetane-3-carboxamido)butanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 19)
Method X-ray diffraction Resolution 2.20 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.504
PHE76
1.343
ASN78
1.334
ARG79
3.347
LEU101
4.997
GLY104
3.064
Residue
Distance (Å)
THR105
3.382
GLY106
3.675
PHE148
3.721
ALA149
3.015
ASN150
3.719
ILE151
2.838
PDB ID: 5NW0      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-(1-acetamidocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 17)
Method X-ray diffraction Resolution 2.30 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.549
PHE76
1.338
ASN78
1.334
ARG79
3.298
GLY104
2.967
THR105
3.237
Residue
Distance (Å)
GLY106
3.423
PHE148
3.554
ALA149
2.942
ASN150
3.751
ILE151
2.835
PDB ID: 6GFZ      pVHL:EloB:EloC in complex with modified VH032 containing (3S,4S)-3-fluoro-4-hydroxyproline (ligand 14b)
Method X-ray diffraction Resolution 2.30 Å Mutation No [7]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.520
PHE76
1.335
ASN78
1.325
ARG79
3.215
GLY104
3.008
THR105
3.221
Residue
Distance (Å)
GLY106
3.615
PHE148
3.712
ALA149
2.894
ASN150
3.678
ILE151
2.820
PDB ID: 4BKT      von Hippel Lindau protein:ElonginB:ElonginC complex, in complex with (2S,4R)-N-methyl-1-[2-(3-methyl-1,2-oxazol-5-yl)ethanoyl]-4-oxidanyl-pyrrolidine-2-carboxamide
Method X-ray diffraction Resolution 2.35 Å Mutation No [6]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
QPIFANITLP
154
VYTLKERCLQ
164

VVRSLVKPEN
174
YRRLDIVRSL
184
YEDLEDHPNV
194
QKDLERL
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:105 or .C:106 or .C:107 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.424
PHE76
1.332
ASN78
1.335
ARG79
3.285
LEU101
4.914
THR105
4.016
Residue
Distance (Å)
GLY106
3.402
ARG107
4.768
PHE148
3.360
ALA149
2.800
ASN150
3.682
ILE151
2.727
PDB ID: 4W9I      pVHL:EloB:EloC in complex with (2S,4R)-1-((2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carbonyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 10)
Method X-ray diffraction Resolution 2.40 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.458
PHE76
1.333
ASN78
1.329
ARG79
3.356
LEU101
4.964
GLY104
3.134
Residue
Distance (Å)
THR105
3.365
GLY106
3.737
PHE148
3.462
ALA149
3.051
ASN150
3.786
ILE151
2.815
PDB ID: 5LLI      pVHL:EloB:EloC in complex with VH298
Method X-ray diffraction Resolution 2.40 Å Mutation No [8]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Q
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.571
PHE76
1.334
ASN78
1.328
ARG79
3.340
GLY104
3.142
THR105
3.359
Residue
Distance (Å)
GLY106
3.652
PHE148
3.649
ALA149
2.964
ASN150
3.824
ILE151
2.870
PDB ID: 6GMX      pVHL:EloB:EloC in complex with 6-chlorothiochroman-4-one
Method X-ray diffraction Resolution 2.53 Å Mutation No [3]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
QPIFANITLP
154
VYTLKERCLQ
164

VVRSLVKPEN
174
YRRLDIVRSL
184
YEDLEDHPNV
194
QKDLERL
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.302
PHE76
1.323
ASN78
1.328
ARG79
3.191
LEU101
4.805
GLY104
3.058
Residue
Distance (Å)
THR105
3.313
GLY106
3.697
PHE148
3.401
ALA149
2.815
ASN150
3.576
ILE151
2.681
PDB ID: 4W9E      pVHL:EloB:EloC in complex with (2S,4R)-1-(3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(thiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 4)
Method X-ray diffraction Resolution 2.60 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.423
PHE76
1.331
ASN78
1.332
ARG79
3.236
LEU101
4.702
GLY104
3.066
Residue
Distance (Å)
THR105
3.295
GLY106
3.668
PHE148
3.755
ALA149
2.965
ASN150
3.751
ILE151
2.858
PDB ID: 4W9G      pVHL:EloB:EloC in complex with (2S,4R)-1-(3,3-dimethylbutanoyl)-4-hydroxy-N-(3-methyl-4-(thiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 6)
Method X-ray diffraction Resolution 2.70 Å Mutation No [4]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.392
PHE76
1.326
ASN78
1.331
ARG79
3.220
LEU101
4.925
GLY104
2.899
Residue
Distance (Å)
THR105
3.218
GLY106
3.786
PHE148
3.542
ALA149
3.062
ASN150
3.755
ILE151
2.802
PDB ID: 5NVZ      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-(1-acetylcyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (ligand 16)
Method X-ray diffraction Resolution 2.70 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Q
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.718
PHE76
1.330
ASN78
1.336
ARG79
3.094
LEU101
4.975
GLY104
3.085
Residue
Distance (Å)
THR105
3.288
GLY106
3.588
PHE148
3.583
ALA149
3.044
ASN150
3.812
ILE151
2.861
PDB ID: 6GFY      pVHL:EloB:EloC in complex with modified VH032 containing (3R,4S)-3-fluoro-4-hydroxyproline (ligand 14a)
Method X-ray diffraction Resolution 2.70 Å Mutation No [7]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.624
PHE76
1.331
ASN78
1.332
ARG79
3.340
LEU101
4.829
GLY104
3.411
Residue
Distance (Å)
THR105
3.315
GLY106
3.906
PHE148
3.601
ALA149
3.115
ASN150
3.891
ILE151
2.945
PDB ID: 6GMQ      pVHL:EloB:EloC in complex with (4-(1H-pyrrol-1-yl)phenyl)methanol
Method X-ray diffraction Resolution 2.75 Å Mutation No [3]
PDB Sequence
LRSVNSREPS
72
QVIFNRSPRV
83
VLPVWLNFDG
93
EPQPYPTLPP
103
GTGRRIHSYR
113

GHLWLFRDAG
123
THDGLLVNQT
133
ELFVPSLNPI
147
FANITLPVYT
157
LKERCLQVVR
167

SLVKPENYRR
177
LDIVRSLYED
187
LEDHPNVQKD
197
LERL
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:104 or .C:105 or .C:106 or .C:107 or .C:148 or .C:149 or .C:150 or .C:151 or .C:157 or .C:158 or .C:159 or .C:160; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.337
PHE76
1.324
ASN78
1.330
ARG79
3.311
GLY104
4.246
THR105
3.233
GLY106
3.068
ARG107
4.489
Residue
Distance (Å)
PHE148
3.469
ALA149
2.897
ASN150
3.175
ILE151
2.719
THR157
3.281
LEU158
2.778
LYS159
2.817
GLU160
4.970
PDB ID: 5NVY      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-acetamidopropanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl) pyrrolidine-2-carboxamide (ligand 11)
Method X-ray diffraction Resolution 2.90 Å Mutation No [5]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.380
PHE76
1.325
ASN78
1.333
ARG79
3.302
LEU101
4.750
GLY104
3.129
Residue
Distance (Å)
THR105
3.252
GLY106
3.921
PHE148
3.796
ALA149
3.101
ASN150
3.639
ILE151
2.855
PDB ID: 6FMJ      pVHL:EloB:EloC in complex with (2S,4R)-1-((S)-2-Acetamidopropanethioyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl) benzyl)pyrrolidine-2-carboxamide (ligand 3)
Method X-ray diffraction Resolution 2.45 Å Mutation No [9]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.491
PHE76
1.333
ASN78
1.330
ARG79
3.255
LEU101
4.769
GLY104
3.105
Residue
Distance (Å)
THR105
3.317
GLY106
3.856
PHE148
3.631
ALA149
3.078
ASN150
3.797
ILE151
2.845
PDB ID: 6FMK      pVHL:EloB:EloC in complex with N-((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamothioyl) pyrrolidin-1-yl)-1-thioxopropan-2-yl)acetamide (ligand 4)
Method X-ray diffraction Resolution 2.75 Å Mutation No [9]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .CAS or .CAS2 or .CAS3 or :3CAS;style chemicals stick;color identity;select .C:75 or .C:76 or .C:78 or .C:79 or .C:101 or .C:104 or .C:105 or .C:106 or .C:148 or .C:149 or .C:150 or .C:151; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
Residue
Distance (Å)
ILE75
3.507
PHE76
1.333
ASN78
1.337
ARG79
3.345
LEU101
4.791
GLY104
3.153
Residue
Distance (Å)
THR105
3.368
GLY106
3.971
PHE148
3.479
ALA149
3.108
ASN150
3.702
ILE151
2.879
PDB ID: 6FMI      pVHL:EloB:EloC in complex with N-((S)-1-((2S,4R)-4-Hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamothioyl) pyrrolidin-1-yl)-1-oxopropan-2-yl)acetamide (ligand 2)
Method X-ray diffraction Resolution 2.80 Å Mutation No [9]
PDB Sequence
VLRSVNSREP
71
SQVIFNRSPR
82
VVLPVWLNFD
92
GEPQPYPTLP
102
PGTGRRIHSY
112

RGHLWLFRDA
122
GTHDGLLVNQ
132
TELFVPSLNV
142
DGQPIFANIT
152
LPVYTLKERC
162

LQVVRSLVKP
172
ENYRRLDIVR
182
SLYEDLEDHP
192
NVQKDLERLT
202
Click to Show 3D Structure of This Binding Site
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Residue
Distance (Å)
ILE75
3.383
PHE76
1.334
ASN78
1.333
ARG79
3.221
GLY104
3.172
THR105
3.322
Residue
Distance (Å)
GLY106
3.962
PHE148
4.085
ALA149
3.018
ASN150
3.786
ILE151
2.872
References  Top
REF 1 Small-molecule inhibitors of the interaction between the E3 ligase VHL and HIF1Alpha. Angew Chem Int Ed Engl. 2012 Nov 12;51(46):11463-7.
REF 2 Dissecting fragment-based lead discovery at the von Hippel-Lindau protein:hypoxia inducible factor 1Alpha protein-protein interface. Chem Biol. 2012 Oct 26;19(10):1300-12.
REF 3 Surface Probing by Fragment-Based Screening and Computational Methods Identifies Ligandable Pockets on the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase. J Med Chem. 2018 Aug 23;61(16):7387-7393.
REF 4 Structure-guided design and optimization of small molecules targeting the protein-protein interaction between the von Hippel-Lindau (VHL) E3 ubiquitin ligase and the hypoxia inducible factor (HIF) alpha subunit with in vitro nanomolar affinities. J Med Chem. 2014 Oct 23;57(20):8657-63.
REF 5 Group-Based Optimization of Potent and Cell-Active Inhibitors of the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase: Structure-Activity Relationships Leading to the Chemical Probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (VH298). J Med Chem. 2018 Jan 25;61(2):599-618.
REF 6 Is NMR Fragment Screening Fine-Tuned to Assess Druggability of Protein-Protein Interactions?. ACS Med Chem Lett. 2014 Jan 9;5(1):23-28.
REF 7 3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted Protein Degradation. J Am Chem Soc. 2018 Jul 25;140(29):9299-9313.
REF 8 Potent and selective chemical probe of hypoxic signalling downstream of HIF-Alpha hydroxylation via VHL inhibition. Nat Commun. 2016 Nov 4;7:13312.
REF 9 Thioamide substitution to probe the hydroxyproline recognition of VHL ligands. Bioorg Med Chem. 2018 Jul 15;26(11):2992-2995.

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