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 = "IUPAC Secretariat",

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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 - http://www.scopus.com/inward/record.url?scp=77956662233&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77956662233&partnerID=8YFLogxK

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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