Isolation and synthesis of (-)-(5S)-2-imino-1-methylpyrrolidine-5-carboxylic acid from Cliona tenuis:: Structure revision of pyrostatins

被引：26

作者：

Castellanos, Leonardo ^{[1
]}

Duque, Carmenza

Zea, Sven

Espada, Alfonso

Rodriguez, Jaime

Jimenez, Carlos

机构：

[1] Univ Nacl Colombia, Dept Quim, Bogota 14490, Colombia

[2] Univ Nacl Colombia, Dept Biol, INVEMAR, Santa Maria 1016, Colombia

[3] Univ Nacl Colombia, Ctr Estudios Ciencias Mar, INVEMAR, Santa Maria 1016, Colombia

[4] Lilly SA, Analyt Technol DCR&T Alcobendas, Alcobendas 28108, Madrid, Spain

[5] Univ A Coruna, Dept Quim Fundamental, Fac Ciencias, E-15071 La Coruna, Spain

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol062087k

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

(-)-(5S)-2-Imino-1-methylpyrrolidine-5-carboxylic acid (1), previously reported as the N-acetyl-beta-D-glucosaminidase inhibitor pyrostatin B, has been isolated from the organic extracts of the burrowing sponge Cliona tenuis. The structure of 1, including its absolute stereochemistry, was characterized from its spectral data and chemical transformations and confirmed by total synthesis. The synthesis of 1 reveals that the structure of pyrostatin B has been incorrectly assigned. Comparison of NMR spectral data strongly suggests that pyrostatins A and B are identical to 5-hydroxyectoine and ectoine, respectively.

引用

页码：4967 / 4970

页数：4

共 27 条

[1]

ANDERSEN RJ, 1978, TETRAHEDRON LETT, P2541

[2]

CLIONAMIDE, A MAJOR METABOLITE OF THE SPONGE CLIONA-CELATA GRANT [J].

ANDERSEN, RJ ;

STONARD, RJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (17) :2325-2328

[3]

PYROSTATIN-A AND PYROSTATIN-B, NEW INHIBITORS OF N-ACETYL-BETA-D-GLUCOSAMINIDASE, PRODUCED BY STREPTOMYCES SP SA-3501 [J].

AOYAMA, T ;

KOJIMA, F ;

IMADA, C ;

MURAOKA, Y ;

NAGANAWA, H ;

OKAMI, Y ;

TAKEUCHI, T ;

AOYAGI, T .

JOURNAL OF ENZYME INHIBITION, 1995, 8 (04) :223-232

[4]

Reaction of azides with dichloroindium hydride: Very mild production of amines and pyrrolidin-2-imines through possible indium-aminyl radicals [J].

Benati, Luisa ;

Bencivenni, Giorgio ;

Leardini, Rino ;

Nanni, Daniele ;

Minozzi, Matteo ;

Spagnolo, Piero ;

Scialpi, Rosanna ;

Zanardi, Giuseppe .

ORGANIC LETTERS, 2006, 8 (12) :2499-2502

[5]

Polychlorinated androstanes from the burrowing sponge Cliona nigricans [J].

Fattorusso, E ;

Taglialatela-Scafati, O ;

Petrucci, F ;

Bavestrello, G ;

Calcinai, B ;

Cerrano, C ;

Di Meglio, P ;

Ianaro, A .

ORGANIC LETTERS, 2004, 6 (10) :1633-1635

[6]

1,4,5,6-TETRAHYDRO-2-METHYL-4-PYRIMIDINECARBOXYLIC ACID - A NOVEL CYCLIC AMINO-ACID FROM HALOPHILIC PHOTOTROPHIC BACTERIA OF THE GENUS ECTOTHIORHODOSPIRA [J].

GALINSKI, EA ;

PFEIFFER, HP ;

TRUPER, HG .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1985, 149 (01) :135-139

[7]

2-iminopyrrolidines as potent and selective inhibitors of human inducible nitric oxide synthase [J].

Hagen, TJ ;

Bergmanis, AA ;

Kramer, SW ;

Fok, KF ;

Schmelzer, AE ;

Pitzele, BS ;

Swenton, L ;

Jerome, GM ;

Kornmeier, CM ;

Moore, WM ;

Branson, LF ;

Connor, JR ;

Manning, PT ;

Currie, MG ;

Hallinan, EA .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (19) :3675-3683

[8]

Enzyme inhibitors and other bioactive compounds from marine actinomycetes [J].

Imada, C .

ANTONIE VAN LEEUWENHOEK INTERNATIONAL JOURNAL OF GENERAL AND MOLECULAR MICROBIOLOGY, 2005, 87 (01) :59-63

[9]

INBAR L, 1988, J BIOL CHEM, V263, P16014

[10]

THE CONFORMATION OF NEW TETRAHYDROPYRIMIDINE DERIVATIVES IN SOLUTION AND IN THE CRYSTAL [J].

INBAR, L ;

FROLOW, F ;

LAPIDOT, A .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1993, 214 (03) :897-906

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