THE SYNTHESIS OF (6R)-[6-H-2]-5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE AND (6S)-[6-H-2]-5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE

被引：8

作者：

BALASUBRAMANIAN, S ^{[1
]}

ABELL, C ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)92131-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(6R)-[6-2H]- and (6S)-[6-2H]5-enolpyruvylshikimate-3-phosphate have been synthesised for the kinetic analysis of the chorismate synthase reaction. The synthesis uses purified shikimate kinase and EPSP synthase for enantiospecific biotransformations and also clarifies the stereochemical course of the Diels Alder reaction in the synthesis of shikimic acid.

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页码：963 / 966

页数：4

相关论文

共 20 条

[11] IMPROVED ASSAY FOR NANOMOLE AMOUNTS OF INORGANIC-PHOSPHATE [J].

LANZETTA, PA ;

ALVAREZ, LJ ;

REINACH, PS ;

CANDIA, OA .

ANALYTICAL BIOCHEMISTRY, 1979, 100 (01) :95-97

[12] A STEREOSPECIFIC TOTAL SYNTHESIS OF D-(-)-SHIKIMIC ACID [J].

MCCRINDLE, R ;

OVERTON, KH ;

RAPHAEL, RA .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR) :1560-1566

[13]

MCCRINDLE R, 1968, TETRAHEDRON LETT, V15, P1847

[14] THE CLONING AND EXPRESSION OF THE AROL GENE FROM ESCHERICHIA-COLI-K12 - PURIFICATION AND COMPLETE AMINO-ACID-SEQUENCE OF SHIKIMATE KINASE-II, THE AROL-GENE PRODUCT [J].

MILLAR, G ;

LEWENDON, A ;

HUNTER, MG ;

COGGINS, JR .

BIOCHEMICAL JOURNAL, 1986, 237 (02) :427-437

[15] STERIC COURSE OF CHORISMATE SYNTHETASE REACTION AND 3-DEOXY-D-ARABINO-HEPTULOSONATE 7-PHOSPHATE (DAHP) SYNTHETASE REACTION [J].

ONDERKA, DK ;

FLOSS, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) :5894-&

[16]

ONDERKA DK, 1972, J BIOL CHEM, V247, P736

[17] A STEREOSPECIFIC SYNTHESIS OF DL-SHIKIMIC ACID [J].

SMISSMAN, EE ;

SUH, JT ;

OXMAN, M ;

DANIELS, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (11) :2909-2910

[18] STEREOSPECIFIC SYNTHESIS OF D(-)-SHIKIMIC ACID1,2 [J].

SMISSMAN, EE ;

SUH, JT ;

DANIELS, R ;

OXMAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (06) :1040-&

[19] SHIKIMATE-DERIVED METABOLITES .14. CHIRAL SYNTHESIS OF "5-ENOLPYRUVYL-SHIKIMATE-3-PHOSPHATE [J].

TENG, CYP ;

YUKIMOTO, Y ;

GANEM, B .

TETRAHEDRON LETTERS, 1985, 26 (01) :21-24

[20]

WEISS U, 1980, BIOSYNTHESIS AROMATI