An efficient approach for monosultide bridge formation in solid-phase peptide synthesis

被引：31

作者：

Campiglia, P

Gomez-Monterrey, I

Longobardo, L

Lama, T

Novellino, E

Grieco, P ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Farmaceut & Tossicol, I-80131 Naples, Italy

[2] Univ Naples Federico II, Dipartimento Sci Alimenti, I-80131 Naples, Italy

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 07期

关键词：

thioether bridge; solid-phase peptide synthesis; macrocyclization;

D O I：

10.1016/j.tetlet.2003.12.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient approach for the synthesis of cyclic peptides containing unnatural thioether side-chain bridges, based on the use of (2 S)-9-fluorenylmethyl-2[(tert-butoxycarbonyl)amino]-4-iodobutanoate and its homologue 5-iodopentanoate, derived from Boc-L-Asp-OFm and Boc-L-Glu-OFm, respectively, is reported. The synthesis was performed by a tandem combination of solid-phase peptide synthesis and microwave-assisted cyclization strategy. (C) 2003 Elsevier Ltd. All rights reserved.

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收藏

页码：1453 / 1456

页数：4

相关论文

共 27 条

[1]

Atherton E., 1989, SOLID PHASE PEPTIDE

[2] AMINO ACID AND PEPTIDE CHEMISTRY .3. SYNTHESIS OF ENANTIOPURE N-PROTECTED AND C-PROTECTED HOMO-BETA-AMINO ACIDS BY DIRECT HOMOLOGATION OF ALPHA-AMINO-ACIDS [J].

CAPUTO, R ;

CASSANO, E ;

LONGOBARDO, L ;

PALUMBO, G .

TETRAHEDRON, 1995, 51 (45) :12337-12350

[3] CHIRAL N-PROTECTED BETA-IODOAMINES FROM ALPHA-AMINO-ACIDS - A GENERAL-SYNTHESIS [J].

CAPUTO, R ;

CASSANO, E ;

LONGOBARDO, L ;

PALUMBO, G .

TETRAHEDRON LETTERS, 1995, 36 (01) :167-168

[4] Microwave parallel library generation:: Comparison of a conventional- and microwave-generated substituted 4(5)-sulfanyl-1H-imidazole library [J].

Coleman, CM ;

MacElroy, JMD ;

Gallagher, JF ;

O'Shea, DF .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (01) :87-93

[5] Synthesis and characterization of cyclic pseudopeptide libraries containing thiomethylene and thiomethylene-sulfoxide amide bond surrogates [J].

Crozet, Y ;

Wen, JJ ;

Loo, RO ;

Andrews, PC ;

Spatola, AF .

MOLECULAR DIVERSITY, 1998, 3 (04) :261-276

[6] Microwave-assisted solid-phase synthesis of 5-carboxamido-N-acetyltryptamine derivatives [J].

Fînaru, A ;

Berthault, A ;

Besson, T ;

Guillaumet, G ;

Berteina-Raboin, S .

ORGANIC LETTERS, 2002, 4 (16) :2613-2615

[7] Rapid and efficient methodology to perform macrocyclization reactions in solid-phase peptide chemistry [J].

Grieco, P ;

Campiglia, P ;

Gomez-Monterrey, I ;

Lama, T ;

Novellino, E .

SYNLETT, 2003, (14) :2216-2218

[8] Lantibiotics and microcins: polypeptides with unusual chemical diversity [J].

Jack, RW ;

Jung, G .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (03) :310-317

[9] Lantibiotics and microcins: Novel posttranslational modifications of polypeptides [J].

Kaiser, D ;

Jack, RW ;

Jung, G .

PURE AND APPLIED CHEMISTRY, 1998, 70 (01) :97-104

[10] High-speed combinatorial synthesis utilizing microwave irradiation [J].

Kappe, CO .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) :314-320