Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters
Abstract A histidine‐containing cyclic dipeptide, cyclo( D ‐Leu‐ L ‐His), was almost 20 times as efficient a catalyst as imidazole in the hydrolysis of p ‐nitrophenyl laurate. The effect of dioxane on the hydrolysis showed that hydrophobic interaction between the cyclic dipeptide and the ester is ve...
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crwiley:10.1002/bip.1977.360161009 2024-06-02T08:05:11+00:00 Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters Imanishi, Yukio Tanihara, Masao Sugihara, Toshiharu Higashimura, Toshinobu 1977 http://dx.doi.org/10.1002/bip.1977.360161009 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fbip.1977.360161009 https://onlinelibrary.wiley.com/doi/pdf/10.1002/bip.1977.360161009 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Biopolymers volume 16, issue 10, page 2203-2215 ISSN 0006-3525 1097-0282 journal-article 1977 crwiley https://doi.org/10.1002/bip.1977.360161009 2024-05-03T10:35:32Z Abstract A histidine‐containing cyclic dipeptide, cyclo( D ‐Leu‐ L ‐His), was almost 20 times as efficient a catalyst as imidazole in the hydrolysis of p ‐nitrophenyl laurate. The effect of dioxane on the hydrolysis showed that hydrophobic interaction between the cyclic dipeptide and the ester is very important. This reaction obeyed the Michaelis‐Menten kinetics, and the Michaelis constant K m was as low as 9.98 × 10 −5 M . Since the linear dipeptide having D ‐Leu‐ L ‐His sequence was nearly inactive in the hydrolysis, the functional groups of cyclo( D ‐Leu‐ L ‐His) in a specific arrangement held by the rigid backbone must have cooperated in the fast hydrolysis. Very weak catalysis by the diasteremeric cyclic dipeptide, cyclo( L ‐Leu‐ L ‐His), in the hydrolysis supported the above view. Article in Journal/Newspaper Carbonic acid Wiley Online Library Biopolymers 16 10 2203 2215 |
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Wiley Online Library |
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English |
description |
Abstract A histidine‐containing cyclic dipeptide, cyclo( D ‐Leu‐ L ‐His), was almost 20 times as efficient a catalyst as imidazole in the hydrolysis of p ‐nitrophenyl laurate. The effect of dioxane on the hydrolysis showed that hydrophobic interaction between the cyclic dipeptide and the ester is very important. This reaction obeyed the Michaelis‐Menten kinetics, and the Michaelis constant K m was as low as 9.98 × 10 −5 M . Since the linear dipeptide having D ‐Leu‐ L ‐His sequence was nearly inactive in the hydrolysis, the functional groups of cyclo( D ‐Leu‐ L ‐His) in a specific arrangement held by the rigid backbone must have cooperated in the fast hydrolysis. Very weak catalysis by the diasteremeric cyclic dipeptide, cyclo( L ‐Leu‐ L ‐His), in the hydrolysis supported the above view. |
format |
Article in Journal/Newspaper |
author |
Imanishi, Yukio Tanihara, Masao Sugihara, Toshiharu Higashimura, Toshinobu |
spellingShingle |
Imanishi, Yukio Tanihara, Masao Sugihara, Toshiharu Higashimura, Toshinobu Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
author_facet |
Imanishi, Yukio Tanihara, Masao Sugihara, Toshiharu Higashimura, Toshinobu |
author_sort |
Imanishi, Yukio |
title |
Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
title_short |
Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
title_full |
Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
title_fullStr |
Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
title_full_unstemmed |
Histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
title_sort |
histidine‐containing cyclic dipeptides as catalysts in the hydrolysis of carbonic acid p‐nitrophenyl esters |
publisher |
Wiley |
publishDate |
1977 |
url |
http://dx.doi.org/10.1002/bip.1977.360161009 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fbip.1977.360161009 https://onlinelibrary.wiley.com/doi/pdf/10.1002/bip.1977.360161009 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
Biopolymers volume 16, issue 10, page 2203-2215 ISSN 0006-3525 1097-0282 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/bip.1977.360161009 |
container_title |
Biopolymers |
container_volume |
16 |
container_issue |
10 |
container_start_page |
2203 |
op_container_end_page |
2215 |
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1800749973128609792 |