BIOSYNTHESIS OF TOLYTOXIN - ORIGIN OF THE CARBONS AND HETEROATOMS

被引：21

作者：

CARMELI, S

MOORE, RE

PATTERSON, GML

YOSHIDA, WY

机构：

[1] UNIV HAWAII, DEPT CHEM, HONOLULU, HI 96822 USA

[2] TEL AVIV UNIV, DEPT CHEM, IL-69978 TEL AVIV, ISRAEL

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)73884-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preliminary studies on the biosynthesis of tolytoxin (1) in the terrestrial blue-green alga Scytonema mirabile BY-8-1 are reported. Incorporation experiments with [1,2-C-13]acetate, [1-C-13, O-18]acetate, [1,2-C-13]glycine, [2-C-13,N-15]glycine and (methyl-C-13]methionine indicate that the carbon chain of tolytoxin is a polyketide assembled from a glycine starter unit and 15 acetate units. The one-carbon branches on the polyketide chain originate from the tetrahydrofolate C1 pool.

引用

收藏

页码：5571 / 5574

页数：4

相关论文

共 28 条

[1] TOLYTOXIN AND NEW SCYTOPHYCINS FROM 3 SPECIES OF SCYTONEMA [J].

CARMELI, S ;

MOORE, RE ;

PATTERSON, GML .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (06) :1533-1542

[2] STRUCTURE OF SWINHOLIDE-A, A NEW MACROLIDE FROM THE MARINE SPONGE THEONELLA-SWINHOEI [J].

CARMELY, S ;

KASHMAN, Y .

TETRAHEDRON LETTERS, 1985, 26 (04) :511-514

[3] APPLICATION OF O-18 INDUCED ISOTOPE EFFECTS IN C-13 NMR-SPECTROSCOPY TO THE BIOSYNTHESIS OF ASTELTOXIN [J].

DEJESUS, AE ;

STEYN, PS ;

VLEGGAAR, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1633-1635

[4] MYCALOLIDES-A - C, HYBRID MACROLIDES OF ULAPUALIDES AND HALICHONDRAMIDE, FROM A SPONGE OF THE GENUS MYCALE [J].

FUSETANI, N ;

YASUMURO, K ;

MATSUNAGA, S ;

HASHIMOTO, K .

TETRAHEDRON LETTERS, 1989, 30 (21) :2809-2812

[5] SPHINXOLIDE, A 26-MEMBERED ANTITUMORAL MACROLIDE ISOLATED FROM AN UNIDENTIFIED PACIFIC NUDIBRANCH [J].

GUELLA, G ;

MANCINI, I ;

CHIASERA, G ;

PIETRA, F .

HELVETICA CHIMICA ACTA, 1989, 72 (02) :237-246

[6] BIOSYNTHESIS OF MACROLIDE ANTIBIOTICS .4. STEREOCHEMISTRY OF HYDROGEN LABELING OF BREFELDIN-A BY [2-H-2(3)]ACETATE [J].

HUTCHINSON, CR ;

KUROBANE, I ;

CANE, DE ;

HASLER, H ;

MCINNES, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2477-2480

[7] SCYTOPHYCINS, CYTOTOXIC AND ANTIMYCOTIC AGENTS FROM THE CYANOPHYTE SCYTONEMA-PSEUDOHOFMANNI [J].

ISHIBASHI, M ;

MOORE, RE ;

PATTERSON, GML ;

XU, CF ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5300-5306

[8] SCYTOPHYCINS FROM A BLUE-GREEN-ALGA BELONGING TO THE NOSTOCACEAE [J].

JUNG, JH ;

MOORE, RE ;

PATTERSON, GML .

PHYTOCHEMISTRY, 1991, 30 (11) :3615-3616

[9] BIOACTIVE MARINE METABOLITES .22. ANTITUMOR MACRODIOLIDES ISOLATED FROM A MARINE SPONGE THEONELLA SP - STRUCTURE REVISION OF MISAKINOLIDE-A [J].

KATO, Y ;

FUSETANI, N ;

MATSUNAGA, S ;

HASHIMOTO, K ;

SAKAI, R ;

HIGA, T ;

KASHMAN, Y .

TETRAHEDRON LETTERS, 1987, 28 (49) :6225-6228

[10] MACROCYCLIC ANTIFUNGAL METABOLITES FROM THE SPANISH DANCER NUDIBRANCH HEXABRANCHUS-SANGUINEUS AND SPONGES OF THE GENUS HALICHONDRIA [J].

KERNAN, MR ;

MOLINSKI, TF ;

FAULKNER, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5014-5020