Enzymes and practical asymmetric synthesis

M. Bhupathy; D. L. Hughes; L. S. Amato; J. J. Bergan; J. L. Leazer; T. C. Lovelace; J. M. McNamara; R. A. Reamer; D. R. Sidler; E. J.J. Grabowski; P. J. Reider; I. Shinkai

doi:10.1351/pac199264121939

Enzymes and practical asymmetric synthesis

M. Bhupathy
, D. L. Hughes
, L. S. Amato
, J. J. Bergan
, J. L. Leazer
, T. C. Lovelace
, J. M. McNamara
, R. A. Reamer
, D. R. Sidler
, E. J.J. Grabowski
, P. J. Reider
, I. Shinkai

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

2 Scopus citations

Abstract

A practical, chemoenzymatic, four-step synthesis of the LTD4 antagonist MK-0679 is described. The key steps are enzymatic hydrolysis of the prochiral diester to the ester-acid in 99% enantiomeric excess followed by aluminum mediated amidation of the methyl ester to afford MK-0679 in high overall yield. This synthesis is superior to the synthesis of the racemate MK-0571.

Original language	English (US)
Pages (from-to)	1939-1944
Number of pages	6
Journal	Pure and Applied Chemistry
Volume	64
Issue number	12
DOIs	https://doi.org/10.1351/pac199264121939
State	Published - Jan 1 1992
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering

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10.1351/pac199264121939

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@article{45eb22ac0cd1441890ed726879312047,

title = "Enzymes and practical asymmetric synthesis",

abstract = "A practical, chemoenzymatic, four-step synthesis of the LTD4 antagonist MK-0679 is described. The key steps are enzymatic hydrolysis of the prochiral diester to the ester-acid in 99\% enantiomeric excess followed by aluminum mediated amidation of the methyl ester to afford MK-0679 in high overall yield. This synthesis is superior to the synthesis of the racemate MK-0571.",

author = "M. Bhupathy and Hughes, \{D. L.\} and Amato, \{L. S.\} and Bergan, \{J. J.\} and Leazer, \{J. L.\} and Lovelace, \{T. C.\} and McNamara, \{J. M.\} and Reamer, \{R. A.\} and Sidler, \{D. R.\} and Grabowski, \{E. J.J.\} and Reider, \{P. J.\} and I. Shinkai",

year = "1992",

month = jan,

day = "1",

doi = "10.1351/pac199264121939",

language = "English (US)",

volume = "64",

pages = "1939--1944",

journal = "Pure and Applied Chemistry",

issn = "0033-4545",

publisher = "Walter de Gruyter GmbH",

number = "12",

}

TY - JOUR

T1 - Enzymes and practical asymmetric synthesis

AU - Bhupathy, M.

AU - Hughes, D. L.

AU - Amato, L. S.

AU - Bergan, J. J.

AU - Leazer, J. L.

AU - Lovelace, T. C.

AU - McNamara, J. M.

AU - Reamer, R. A.

AU - Sidler, D. R.

AU - Grabowski, E. J.J.

AU - Reider, P. J.

AU - Shinkai, I.

PY - 1992/1/1

Y1 - 1992/1/1

N2 - A practical, chemoenzymatic, four-step synthesis of the LTD4 antagonist MK-0679 is described. The key steps are enzymatic hydrolysis of the prochiral diester to the ester-acid in 99% enantiomeric excess followed by aluminum mediated amidation of the methyl ester to afford MK-0679 in high overall yield. This synthesis is superior to the synthesis of the racemate MK-0571.

AB - A practical, chemoenzymatic, four-step synthesis of the LTD4 antagonist MK-0679 is described. The key steps are enzymatic hydrolysis of the prochiral diester to the ester-acid in 99% enantiomeric excess followed by aluminum mediated amidation of the methyl ester to afford MK-0679 in high overall yield. This synthesis is superior to the synthesis of the racemate MK-0571.

UR - https://www.scopus.com/pages/publications/77956662233

UR - https://www.scopus.com/pages/publications/77956662233#tab=citedBy

U2 - 10.1351/pac199264121939

DO - 10.1351/pac199264121939

M3 - Article

AN - SCOPUS:77956662233

SN - 0033-4545

VL - 64

SP - 1939

EP - 1944

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 12

ER -

Enzymes and practical asymmetric synthesis

Abstract

All Science Journal Classification (ASJC) codes

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