Chemo-enzymatic synthesis of isotopically labelled L-valine, L-isoleucine and allo-isoleucine

被引：20

作者：

Kelly, NM

Reid, RG

Willis, CL

Winton, PL

机构：

[1] UNIV BRISTOL,SCH CHEM,BRISTOL BS8 1TS,AVON,ENGLAND

[2] AMERSHAM INT PLC,CARDIFF CF4 7YT,S GLAM,WALES

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/0040-4039(96)00053-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of (3R)-[4,4,4-D-3]-L-valine, [N-15]-L-isoleucine and [N-15]-allo-isoleucine from homochiral 2-alkylated carboxylic acids are described, The approach involves a one-carbon homologation of the carboxylic acid to give the corresponding beta-substituted alpha-keto ester which is converted directly to the alpha-amino acid in a one-pot procedure involving two enzyme catalysed reactions (Candida cylindracea lipase to hydrolyse the ester and leucine dehydrogenase to catalyse the reductive amination of the ketone). This strategy may be simply adapted for the selective labelling of each site of the L-amino acid.

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页码：1517 / 1520

页数：4

相关论文

共 16 条

[1] AN EFFICIENT SYNTHESIS OF NOVEL ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES [J].

ANGELASTRO, MR ;

PEET, NP ;

BEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3913-3916

[2] SYNTHESIS OF (2(R),3(S))[4-H-2(3)]VALINE - APPLICATION TO THE STUDY OF THE RING EXPANSION OF PENICILLIN-N BY DEACETOXYCEPHALOSPORIN-C SYNTHASE FROM STREPTOMYCES-CLAVULIGERUS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CROUCH, NP ;

MELLOR, LC ;

MORGAN, N ;

SMITH, AM ;

SUTHERLAND, JD .

TETRAHEDRON, 1995, 51 (14) :4089-4100

[3] CEPHALOSPORIN-C BIOSYNTHESIS - STEREOCHEMISTRY OF THE INCORPORATION OF D,L,D-ALPHA-AMINODIPOYL-CYSTEINYL-(3S)-[2-2H,4-C-13]VALINE INTO BETA-LACTAM COMPOUNDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CROUCH, NP ;

TURNER, NJ ;

SCHOFIELD, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) :1141-1143

[4] ENANTIOSELECTIVE SYNTHESES OF (S)-3-HYDROXYPYRROLIDIN-2-ONE AND (R)-3-HYDROXYPYRROLIDIN-2-ONE VIA LACTATE-DEHYDROGENASE CATALYZED REDUCTIONS OF 4-BENZYLOXYCARBONYLAMINO-2-OXOBUTANOIC ACID [J].

BENTLEY, JM ;

WADSWORTH, HJ ;

WILLIS, CL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :231-232

[5]

CHELINZTEV VV, 1929, BER DTSCH CHEM GES B, V62, P2210

[6] 1,3-DIASTEREOCONTROL WITH BROMOALLENES - SYNTHESIS OF ENANTIOMERICALLY PURE BETA-BRANCHED ALPHA-AMINO-ACIDS [J].

DANIELLO, F ;

MANN, A ;

TADDEI, M ;

WERMUTH, CG .

TETRAHEDRON LETTERS, 1994, 35 (42) :7775-7778

[7] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[8] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA .

TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144

[9] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[10] EFFICIENT SYNTHESIS OF DIASTEREOSELECTIVELY LABELED (3S)-[4-C-13]-L-VALINE, AND REGIOSELECTIVELY LABELED [3-(CH3)-C-13]-L-ISOLEUCINE HYDROCHLORIDES [J].

HUMPHREY, JM ;

HART, JA ;

CHAMBERLIN, AR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (12) :1315-1320