SYNTHESIS OF D-(-)-[1,7-(C-13)2]SHIKIMIC ACID

被引：16

作者：

CHO, HJ

HEIDE, L

FLOSS, HG

机构：

[1] UNIV WASHINGTON,DEPT CHEM,BG-10,SEATTLE,WA 98195

[2] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 1992年 / 31卷 / 08期

关键词：

C-13; LABELING; CHEMICAL SYNTHESIS; SHIKIMIC ACID; OPTICALLY ACTIVE;

D O I：

10.1002/jlcr.2580310804

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The chemical synthesis of 99% enriched D(-)-[1,7-C-13(2)]shikimic acid from [1,2-C-13(2)]acetate in 25% overall yield is described. A two-carbon phosphonate synthon was prepared from [1,2-C-13(2)]acetate and used in the shikimate synthesis of Fleet and coworkers.

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页码：589 / 594

页数：6

相关论文

共 9 条

[1] BIOSYNTHESIS OF ANSATRIENIN - NONINCORPORATION OF SHIKIMIC ACID INTO THE MC7N UNIT AND STEREOCHEMISTRY OF ITS CONVERSION TO THE CYCLOHEXANECARBOXYLIC ACID MOIETY [J].

CASATI, R ;

BEALE, JM ;

FLOSS, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :8102-8104

[2]

CHO H, 1990, THESIS OHIO STATE U

[3] ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE [J].

FLEET, GWJ ;

SHING, TKM ;

WARR, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :905-908

[4] SHIKIMATE-DERIVED METABOLITES .4. FROM GLUCOSE TO AROMATICS - RECENT DEVELOPMENTS IN NATURAL-PRODUCTS OF SHIKIMIC ACID PATHWAY [J].

GANEM, B .

TETRAHEDRON, 1978, 34 (23) :3353-3383

[5]

Haslam E., 1974, SHIKIMATE PATHWAY

[6]

HASSNER A, 1978, TETRAHEDRON LETT, V19, P4475

[7] EPIMERIZATION OF ALDOSES BY MOLYBDATE INVOLVING A NOVEL REARRANGEMENT OF THE CARBON SKELETON [J].

HAYES, ML ;

PENNINGS, NJ ;

SERIANNI, AS ;

BARKER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6764-6769

[8] INCORPORATION OF SHIKIMIC ACID INTO P-HYDROXYBENZOIC ACID IN LITHOSPERMUM-ERYTHRORHIZON CELL-CULTURES [J].

HEIDE, L ;

FLOSS, HG ;

TABATA, M .

PHYTOCHEMISTRY, 1989, 28 (10) :2643-2645

[9] 2',3',5'-TRI-O-BENZOYL[4-C-13]URIDINE - EFFICIENT, REGIOSPECIFIC SYNTHESIS OF PYRIMIDINE RING [J].

ROBERTS, JL ;

POULTER, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1547-1555