ENZYME-CATALYZED HYDROLYSES OF SOME MESO-DIESTERS

被引：21

作者：

COTTERILL, IC

COX, PB

DRAKE, AF

LEGRAND, DM

HUTCHINSON, EJ

LATOUCHE, R

PETTMAN, RB

PRYCE, RJ

ROBERTS, SM ^{[1
]}

RYBACK, G

SIK, V

WILLIAMS, JO

机构：

[1] UNIV EXETER,DEPT CHEM,EXETER EX4 4RJ,DEVON,ENGLAND

[2] UNIV LONDON BIRKBECK COLL,DEPT CHEM,LONDON WC1H 0AJ,ENGLAND

[3] SHELL RES LTD,SITTINGBOURNE RES CTR,SITTINGBOURNE ME9 8AG,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期

关键词：

D O I：

10.1039/p19910003071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diester 7 is hydrolysed, using porcine pancreatic lipase as catalyst, to give the monoester 8. The latter compound has been converted into the known azido alcohol 9 and into the purine derivative 10. Pig liver esterase (ple) catalysed hydrolysis of the diester 11 gave the acid 13 not the enantiomer 12 as previously reported. The structure of 13 was determined by its conversion into the compound ent-10. The diesters 17 and 18 are converted into the mono-esters 20 and 21 respectively using ple: hydrolysis of the diester 16 yields a mono-acid of high optical purity. The structure of this mono-acid is believed to be that shown in formula 19.

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页码：3071 / 3075

页数：5

相关论文

共 18 条

[1] ENANTIOMERIC EXCESS AND ABSOLUTE-CONFIGURATION DETERMINATION OF CIS-DIHYDRODIOLS FROM BACTERIAL METABOLISM OF MONOCYCLIC ARENES [J].

BOYD, DR ;

DORRITY, MRJ ;

HAND, MV ;

MALONE, JF ;

SHARMA, ND ;

DALTON, H ;

GRAY, DJ ;

SHELDRAKE, GN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :666-667

[2] DIELS-ALDER REACTIONS INVOLVING CIS-1,2-ISOPROPYLIDENEDIOXYCYCLOHEXA-3,5-DIENE AND ENZYMATIC RESOLUTION OF ONE OF THE ADDUCTS [J].

COTTERILL, IC ;

ROBERTS, SM ;

WILLIAMS, JO .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1628-1629

[3]

COX P, UNPUB

[4] RECENT ADVANCES IN THE GENERATION OF CHIRAL INTERMEDIATES USING ENZYMES [J].

DAVIES, HG ;

GREEN, RH ;

KELLY, DR ;

ROBERTS, SM .

CRITICAL REVIEWS IN BIOTECHNOLOGY, 1990, 10 (02) :129-153

[5]

DAVIS HG, 1989, BIOTRANSFORMATIONS P, P25

[6] A HIGHLY ENANTIOSELECTIVE HYDROLYSIS OF CIS-3,5-DIACETOXYCYCLOPENT-1-ENE - AN ENZYMATIC PREPARATION OF 3(R)-ACETOXY-5(S)-HYDROXYCYCLOPENT-1-ENE [J].

DEARDORFF, DR ;

MATTHEWS, AJ ;

MCMEEKIN, DS ;

CRANEY, CL .

TETRAHEDRON LETTERS, 1986, 27 (11) :1255-1256

[7] TRIPLY CONVERGENT SYNTHESIS OF (-)-PROSTAGLANDIN-E2 [J].

JOHNSON, CR ;

PENNING, TD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5655-5656

[8]

JOHNSON CR, 1988, J AM CHEM SOC, V110, P4727

[9] ENZYMES IN ORGANIC-SYNTHESIS .33. STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSES OF MESO-CYCLOPENTYL-1,3-DIESTERS, TETRAHYDROFURANYL-1,3-DIESTERS, AND TETRAHYDROTHIOPHENYL-1,3-DIESTERS [J].

JONES, JB ;

HINKS, RS ;

HULTIN, PG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (02) :452-456

[10] SYNTHESIS AND ANTIVIRAL EVALUATION OF 6'-SUBSTITUTED ARISTEROMYCINS - POTENTIAL MECHANISM-BASED INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE [J].

MADHAVAN, GVB ;

MCGEE, DPC ;

RYDZEWSKI, RM ;

BOEHME, R ;

MARTIN, JC ;

PRISBE, EJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1798-1804