The absolute stereochemistry of anachelins, siderophores from the cyanobacterium Anabaena cylindrica

被引：39

作者：

Ito, Y ^{[1
]}

Ishida, K ^{[1
]}

Okada, S ^{[1
]}

Murakami, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Agr & Life Sci, Marine Biochem Lab, Bunkyo Ku, Tokyo 1138657, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 41期

基金：

日本学术振兴会;

关键词：

anachelin; siderophore; iron; cyanobacteria; Anabaena cylindrica;

D O I：

10.1016/j.tet.2004.07.105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute stereochemistry of anachelins (1 and 2), siderophores isolated from the freshwater cyanobacterium Anabaena cylindrica, was determined via the application of Boc-phenylglycine and Mosher's method. Consequently, it was revealed that a 1,1-dimethyl-3-amino-1,2,3,4-tetrahydro-6,7-dihydroxyquinolinium unit (Dmaq) has 3S (eq.) configuration, and a 6-amino-3,5,7-trihydroxy-heptanoic acid unit (Atha) has 3R, 5S, 6S configuration. The 6S configuration of Atha suggested that L-Ser was a biosynthetic precursor of Atha. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9075 / 9080

页数：6

共 22 条

[1]

Beiderbeck H, 2000, Z NATURFORSCH C, V55, P681

[2]

Bockmann M, 1997, Z NATURFORSCH C, V52, P319

[3] SECONDARY METABOLITES FROM FLUORESCENT PSEUDOMONADS [J].

BUDZIKIEWICZ, H .

FEMS MICROBIOLOGY LETTERS, 1993, 104 (3-4) :209-228

[4]

Drechsel H, 1998, J PEPT SCI, V4, P147, DOI 10.1002/(SICI)1099-1387(199805)4:3<147::AID-PSC136>3.3.CO

[5]

2-3

[6] THE STEREOCHEMISTRY OF AN OXAZOLINE DERIVATIVE OF THREONINE - IMPROVEMENT OF A RECENT THREONINE SYNTHESIS [J].

ELLIOTT, DF .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (MAR) :589-594

[7] NUCLEAR MAGNETIC-RESONANCE STUDY OF STEREOISOMERIC 2-OXAZOLIDONE AND 2-PHENYL-2-OXAZOLINE DERIVATIVES OF ALPHA-AMINO-BETA-HYDROXY ACIDS [J].

FUTAGAWA, S ;

INUI, T ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (10) :3308-3310

[8] Reconstitution and characterization of the Escherichia coli enterobactin synthetase from EntB, EntE, and EntF [J].

Gehring, AM ;

Mori, I ;

Walsh, CT .

BIOCHEMISTRY, 1998, 37 (08) :2648-2659

[9]

GRIFFITHS GL, 1984, J BIOL CHEM, V259, P383

[10]

HASHIMOTO N, 1981, CHEM PHARM BULL, V29, P1475

← 1 2 3 →