Unusual Four-Bond Secondary H/D Isotope Effect Supports a Short−Strong Hydrogen Bond between Phospholipase A2and a Transition State Analogue Inhibitor†

Chunhua Yuan; Shengjiang Tu; Michael H. Gelb; Ming-Daw Tsai

doi:10.1021/bi047503s

Unusual Four-Bond Secondary H/D Isotope Effect Supports a Short−Strong Hydrogen Bond between Phospholipase A2and a Transition State Analogue Inhibitor†

Biochemistry ◽

10.1021/bi047503s ◽

2005 ◽

Vol 44 (12) ◽

pp. 4748-4754 ◽

Cited By ~ 3

Author(s):

Chunhua Yuan ◽

Shengjiang Tu ◽

Michael H. Gelb ◽

Ming-Daw Tsai

Keyword(s):

Hydrogen Bond ◽

Transition State ◽

Isotope Effect ◽

Strong Hydrogen Bond ◽

Transition State Analogue

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Evidence for a Strong Hydrogen Bond in the Catalytic Dyad of Transition-State Analogue Inhibitor Complexes of Chymotrypsin from Proton−Triton NMR Isotope Shifts

Journal of the American Chemical Society ◽

10.1021/ja017860f ◽

2002 ◽

Vol 124 (16) ◽

pp. 4196-4197 ◽

Cited By ~ 19

Author(s):

William M. Westler ◽

Perry A. Frey ◽

Jing Lin ◽

David E. Wemmer ◽

Hiromi Morimoto ◽

...

Keyword(s):

Hydrogen Bond ◽

Transition State ◽

Strong Hydrogen Bond ◽

Isotope Shifts ◽

Transition State Analogue ◽

Catalytic Dyad

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Atomic Dissection of the Hydrogen Bond Network for Transition-State Analogue Binding to Purine Nucleoside Phosphorylase†

Biochemistry ◽

10.1021/bi026636f ◽

2002 ◽

Vol 41 (49) ◽

pp. 14489-14498 ◽

Cited By ~ 41

Author(s):

Greg A. Kicska ◽

Peter C. Tyler ◽

Gary B. Evans ◽

Richard H. Furneaux ◽

Wuxian Shi ◽

...

Keyword(s):

Hydrogen Bond ◽

Transition State ◽

Purine Nucleoside Phosphorylase ◽

Purine Nucleoside ◽

Hydrogen Bond Network ◽

Nucleoside Phosphorylase ◽

Transition State Analogue ◽

Bond Network

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An equilibrium isotope effect due to a strong hydrogen bond

Chemical Physics Letters ◽

10.1016/j.cplett.2018.10.023 ◽

2018 ◽

Vol 713 ◽

pp. 117-120 ◽

Cited By ~ 1

Author(s):

Hai Xu ◽

Ting Luo ◽

Han Wu ◽

Lv-Bing Yuan ◽

Si-Qi Zhao ◽

...

Keyword(s):

Hydrogen Bond ◽

Isotope Effect ◽

Strong Hydrogen Bond

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ChemInform Abstract: Crystal Structure of Thiamin Thiazolone: A Possible Transition-State Analogue with an Intramolecular N-H···O Hydrogen Bond in the V Form

ChemInform ◽

10.1002/chin.198712069 ◽

1987 ◽

Vol 18 (12) ◽

Author(s):

W. SHIN ◽

Y. C. KIM

Keyword(s):

Crystal Structure ◽

Hydrogen Bond ◽

Transition State ◽

Transition State Analogue

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Comment on “An equilibrium isotope effect due to a strong hydrogen bond”

Chemical Physics Letters ◽

10.1016/j.cplett.2019.06.027 ◽

2019 ◽

Vol 730 ◽

pp. 302-305

Author(s):

Daniel J. O'Leary

Keyword(s):

Hydrogen Bond ◽

Isotope Effect ◽

Strong Hydrogen Bond

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The Deuterium Isotope Effect on the NMR Signal of the Low-Barrier Hydrogen Bond in a Transition- State Analog Complex of Chymotrypsin

Biochemical and Biophysical Research Communications ◽

10.1006/bbrc.2000.2986 ◽

2000 ◽

Vol 273 (2) ◽

pp. 789-792 ◽

Cited By ~ 22

Author(s):

Constance S. Cassidy ◽

Jing Lin ◽

Perry A. Frey

Keyword(s):

Hydrogen Bond ◽

Transition State ◽

Isotope Effect ◽

Deuterium Isotope Effect ◽

Transition State Analog

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Correlations of the Basicity of His 57 with Transition State Analogue Binding, Substrate Reactivity, and the Strength of the Low-Barrier Hydrogen Bond in Chymotrypsin†

Biochemistry ◽

10.1021/bi980278s ◽

1998 ◽

Vol 37 (34) ◽

pp. 11940-11948 ◽

Cited By ~ 44

Author(s):

Jing Lin ◽

Constance S. Cassidy ◽

Perry A. Frey

Keyword(s):

Hydrogen Bond ◽

Transition State ◽

Transition State Analogue ◽

Substrate Reactivity ◽

Binding Substrate

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Faculty Opinions recommendation of Selective stabilization of the chorismate mutase transition state by a positively charged hydrogen bond donor.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1012843.187412 ◽

2003 ◽

Author(s):

Arieh Warshel

Keyword(s):

Hydrogen Bond ◽

Transition State ◽

Chorismate Mutase ◽

Hydrogen Bond Donor ◽

Selective Stabilization ◽

Positively Charged

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Faculty Opinions recommendation of L-Enantiomers of transition state analogue inhibitors bound to human purine nucleoside phosphorylase.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1097544.553622 ◽

2008 ◽

Author(s):

Wayne Guida

Keyword(s):

Transition State ◽

Purine Nucleoside Phosphorylase ◽

Purine Nucleoside ◽

Nucleoside Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

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Hydrogen bonds in N-(3-chloro-2-benzo[b]thienocarbonyl)- and N-(2-benzo[b]thienocarbonyl)-N'-monosubstituted thioureas

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19872673 ◽

1987 ◽

Vol 52 (11) ◽

pp. 2673-2679 ◽

Cited By ~ 1

Author(s):

Oľga Hritzová ◽

Peter Kutschy ◽

Ján Imrich ◽

Thomas Schöffmann

Keyword(s):

Hydrogen Bond ◽

Hydrogen Bonds ◽

Strong Hydrogen Bond ◽

Cyclic Form ◽

Thiourea Derivatives

N-(3-Chloro-2-benzo[b]thienocarbonyl)-N'-monosubstituted thiourea derivatives undergo photocyclizations with lower yields than those obtained from analogous N',N'-disubstituted derivatives. This decreased reactivity is caused by the existence of a six-membered cyclic form with the very strong hydrogen bond NH···O=C. The possibility of formation of various conformers has been found with N-(2-benzo[b]thienocarbonyl)-N'-monosubstituted thiourea derivatives as a consequence of the rotation around the C(2)-C(O) connecting line.

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