N-(Hydroxyaminocarbonyl)phenylalanine: A novel class of inhibitor for carboxypeptidase A

Sang J. Chung; Dong H. Kim

doi:10.1016/S0968-0896(00)00235-2

N-(Hydroxyaminocarbonyl)phenylalanine: A novel class of inhibitor for carboxypeptidase A

Sang J. Chung
, Dong H. Kim

Pohang University of Science and Technology

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

20 Scopus citations

Abstract

N-(Hydroxyaminocarbonyl)phenylalanine (1) was designed rationally as a new type of inhibitor for carboxypeptidase A (CPA). The designed inhibitor was readily prepared from phenylalnine benzyl ester in two steps and evaluated to find that rac-1 inhibits CPA in a competitive fashion with the K_i value of 2.09 μM. Surprisingly, inhibitor 1 having the D-configuration is more potent (K_i=1.54 μM) than its antipode by about 3-fold. A possible explanation for the stereochemistry observed in the inhibition of CPA with 1 is presented.

Original language	English
Pages (from-to)	185-189
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	9
Issue number	1
DOIs	https://doi.org/10.1016/S0968-0896(00)00235-2
State	Published - 2001
Externally published	Yes

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title = "N-(Hydroxyaminocarbonyl)phenylalanine: A novel class of inhibitor for carboxypeptidase A",

abstract = "N-(Hydroxyaminocarbonyl)phenylalanine (1) was designed rationally as a new type of inhibitor for carboxypeptidase A (CPA). The designed inhibitor was readily prepared from phenylalnine benzyl ester in two steps and evaluated to find that rac-1 inhibits CPA in a competitive fashion with the Ki value of 2.09 μM. Surprisingly, inhibitor 1 having the D-configuration is more potent (Ki=1.54 μM) than its antipode by about 3-fold. A possible explanation for the stereochemistry observed in the inhibition of CPA with 1 is presented.",

author = "Chung, \{Sang J.\} and Kim, \{Dong H.\}",

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T1 - N-(Hydroxyaminocarbonyl)phenylalanine

T2 - A novel class of inhibitor for carboxypeptidase A

AU - Chung, Sang J.

AU - Kim, Dong H.

PY - 2001

Y1 - 2001

N2 - N-(Hydroxyaminocarbonyl)phenylalanine (1) was designed rationally as a new type of inhibitor for carboxypeptidase A (CPA). The designed inhibitor was readily prepared from phenylalnine benzyl ester in two steps and evaluated to find that rac-1 inhibits CPA in a competitive fashion with the Ki value of 2.09 μM. Surprisingly, inhibitor 1 having the D-configuration is more potent (Ki=1.54 μM) than its antipode by about 3-fold. A possible explanation for the stereochemistry observed in the inhibition of CPA with 1 is presented.

AB - N-(Hydroxyaminocarbonyl)phenylalanine (1) was designed rationally as a new type of inhibitor for carboxypeptidase A (CPA). The designed inhibitor was readily prepared from phenylalnine benzyl ester in two steps and evaluated to find that rac-1 inhibits CPA in a competitive fashion with the Ki value of 2.09 μM. Surprisingly, inhibitor 1 having the D-configuration is more potent (Ki=1.54 μM) than its antipode by about 3-fold. A possible explanation for the stereochemistry observed in the inhibition of CPA with 1 is presented.

UR - https://www.scopus.com/pages/publications/0035180105

U2 - 10.1016/S0968-0896(00)00235-2

DO - 10.1016/S0968-0896(00)00235-2

M3 - Article

C2 - 11197339

AN - SCOPUS:0035180105

SN - 0968-0896

VL - 9

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EP - 189

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 1

ER -

N-(Hydroxyaminocarbonyl)phenylalanine: A novel class of inhibitor for carboxypeptidase A

Abstract

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