Revisiting the effect of water content on enzymatic peptide synthesis in non-aqueous medium

Jong Shik Shin; Byung Gee Kim

doi:10.1023/A:1020952109068

Revisiting the effect of water content on enzymatic peptide synthesis in non-aqueous medium

Jong Shik Shin, Byung Gee Kim

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Enzymatic acyl-transfer reaction in organic medium competes with the hydrolytic side reaction depending on the water content. The effect of water content on aminolysis activity of α-chymotrypsin for the synthesis of Bz-Tyr-Val-NH₂ in acetonitrile was examined under the conditions which were devoid of the hydrolytic deacylation. Excess H-Val-NH₂ (880 mM) was employed to keep the hydrolysis negligible. The aminolysis rate increased abruptly between 4 and 5% (v/v) water but a further increase in the water content did not affect the reaction rate. This suggests that water added more than 5% (v/v) does not enhance intrinsic enzyme activity but acts only as a nucleophile for the hydrolytic deacylation.

Original language	English
Pages (from-to)	1903-1905
Number of pages	3
Journal	Biotechnology Letters
Volume	24
Issue number	22
DOIs	https://doi.org/10.1023/A:1020952109068
Publication status	Published - 2002 Nov

Bibliographical note

Funding Information:
This work was partially supported by the Nano Bioelectronics & Systems Research Center at Seoul National University, and the Advanced Backbone IT Technology Development Project (IMT2000-B3-2) from the Korean Ministry of Information and Communication.

All Science Journal Classification (ASJC) codes

Biotechnology
Bioengineering
Applied Microbiology and Biotechnology

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title = "Revisiting the effect of water content on enzymatic peptide synthesis in non-aqueous medium",

abstract = "Enzymatic acyl-transfer reaction in organic medium competes with the hydrolytic side reaction depending on the water content. The effect of water content on aminolysis activity of α-chymotrypsin for the synthesis of Bz-Tyr-Val-NH2 in acetonitrile was examined under the conditions which were devoid of the hydrolytic deacylation. Excess H-Val-NH2 (880 mM) was employed to keep the hydrolysis negligible. The aminolysis rate increased abruptly between 4 and 5% (v/v) water but a further increase in the water content did not affect the reaction rate. This suggests that water added more than 5% (v/v) does not enhance intrinsic enzyme activity but acts only as a nucleophile for the hydrolytic deacylation.",

author = "Shin, {Jong Shik} and Kim, {Byung Gee}",

note = "Funding Information: This work was partially supported by the Nano Bioelectronics & Systems Research Center at Seoul National University, and the Advanced Backbone IT Technology Development Project (IMT2000-B3-2) from the Korean Ministry of Information and Communication.",

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doi = "10.1023/A:1020952109068",

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AU - Shin, Jong Shik

AU - Kim, Byung Gee

N1 - Funding Information: This work was partially supported by the Nano Bioelectronics & Systems Research Center at Seoul National University, and the Advanced Backbone IT Technology Development Project (IMT2000-B3-2) from the Korean Ministry of Information and Communication.

PY - 2002/11

Y1 - 2002/11

N2 - Enzymatic acyl-transfer reaction in organic medium competes with the hydrolytic side reaction depending on the water content. The effect of water content on aminolysis activity of α-chymotrypsin for the synthesis of Bz-Tyr-Val-NH2 in acetonitrile was examined under the conditions which were devoid of the hydrolytic deacylation. Excess H-Val-NH2 (880 mM) was employed to keep the hydrolysis negligible. The aminolysis rate increased abruptly between 4 and 5% (v/v) water but a further increase in the water content did not affect the reaction rate. This suggests that water added more than 5% (v/v) does not enhance intrinsic enzyme activity but acts only as a nucleophile for the hydrolytic deacylation.

AB - Enzymatic acyl-transfer reaction in organic medium competes with the hydrolytic side reaction depending on the water content. The effect of water content on aminolysis activity of α-chymotrypsin for the synthesis of Bz-Tyr-Val-NH2 in acetonitrile was examined under the conditions which were devoid of the hydrolytic deacylation. Excess H-Val-NH2 (880 mM) was employed to keep the hydrolysis negligible. The aminolysis rate increased abruptly between 4 and 5% (v/v) water but a further increase in the water content did not affect the reaction rate. This suggests that water added more than 5% (v/v) does not enhance intrinsic enzyme activity but acts only as a nucleophile for the hydrolytic deacylation.

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Revisiting the effect of water content on enzymatic peptide synthesis in non-aqueous medium

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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