THE SYNTHESIS OF ISOTOPICALLY LABELED N-ACETYLCYSTEAMINE THIOESTERS UTILIZING A BAKERS-YEAST REDUCTION IN D2O

被引：7

作者：

DILLON, MP

HAYES, MA

SIMPSON, TJ

SWEENEY, JB

机构：

[1] School of Chemistry, University of Bristol, Bristol, BS8 1TS, Cantocks Close

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1991年 / 1卷 / 04期

关键词：

D O I：

10.1016/S0960-894X(00)80257-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Bakers' yeast reduction of ethyl acetoacetate and ethyl 3-oxo-hexanoate in D2O gives the corresponding beta-hydroxy esters bearing an isotopic label at the activated methylene position, in good yield and high enantiomeric excess. These compounds have been converted to their N-acetylcysteamine thioesters for use in biosynthetic studies.

引用

收藏

页码：223 / 226

页数：4

相关论文

共 13 条

[1] MACROLIDE BIOSYNTHESIS .4. INTACT INCORPORATION OF A CHAIN-ELONGATION INTERMEDIATE INTO ERYTHROMYCIN [J].

CANE, DE ;

YANG, CC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1255-1257

[2] MACROLIDE BIOSYNTHESIS .5. INTACT INCORPORATION OF A CHAIN-ELONGATION INTERMEDIATE INTO NARGENICIN [J].

CANE, DE ;

OTT, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4840-4841

[3] SYNTHESIS OF (2S)-2-PROPYLTHIETAN [J].

CRUMP, DR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (09) :1945-1948

[4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[5]

NEUBAUER O, 1910, PHYSIOL CHEM PHYS M, V70, P326

[6]

Neuberg C, 1921, BIOCHEM Z, V115, P282

[7]

Osign, 1990, TATH, V1

[8] STERIC COURSE OF THE ALLYLIC REARRANGEMENT CATALYZED BY BETA-HYDROXYDECANOYLTHIOESTER DEHYDRASE - MECHANISTIC IMPLICATIONS [J].

SCHWAB, JM ;

KLASSEN, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7217-7227

[9] BIOSYNTHESIS OF LONG-CHAIN FATTY-ACIDS - INCORPORATION OF RADIOACTIVITY FROM STEREOSPECIFICALLY TRITIATED MALONYL THIOL ESTERS, AND STEREOCHEMISTRY OF ACETYL-COA CARBOXYLASE REACTION [J].

SEDGWICK, B ;

CORNFORTH, JW ;

FRENCH, SJ ;

GRAY, RT ;

KELSTRUP, E ;

WILLADSEN, P .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1977, 75 (02) :481-495

[10]

Seebach D., 1985, ORG SYNTH, V63, P1