Synthesis of a selenocysteine-containing peptide by native chemical ligation

被引：177

作者：

Gieselman, MD ^{[1
]}

Xie, LL ^{[1
]}

van der Donk, WA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 09期

关键词：

D O I：

10.1021/ol015712o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Sep methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine, Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.

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页码：1331 / 1334

页数：4

相关论文

共 54 条

[11] SYNTHETIC STUDY ON PEPTIDE ANTIBIOTIC NISIN .5. TOTAL SYNTHESIS OF NISIN [J].

FUKASE, K ;

KITAZAWA, M ;

SANO, A ;

SHIMBO, K ;

HORIMOTO, S ;

FUJITA, H ;

KUBO, A ;

WAKAMIYA, T ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (08) :2227-2240

[12] ORGANIC SULFUR CHEMISTRY .10. SELECTIVE DESULFURIZATION OF DISULFIDES - SCOPE AND MECHANISM [J].

HARPP, DN ;

GLEASON, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (10) :2437-+

[13] ORGANIC SULFUR CHEMISTRY .I. DISULFIDE-PHOSPHINE REACTION . DESULFURIZATION WITH TRIS(DIETHYLAMINO)PHOSPHINE [J].

HARPP, DN ;

GLEASON, JG ;

SNYDER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (15) :4181-&

[14] beta-phenylselenoalanine as a dehydroalanine precursor-efficient synthesis of alternariolide (AM-toxin I) [J].

Hashimoto, K ;

Sakai, M ;

Okuno, T ;

Shirahama, H .

CHEMICAL COMMUNICATIONS, 1996, (10) :1139-1140

[15] COMPARISON OF CHEMICAL PROPERTIES OF SELENOCYSTEINE AND SELENOCYSTINE WITH THEIR SULFUR ANALOGS [J].

HUBER, RE ;

CRIDDLE, RS .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1967, 122 (01) :164-&

[16] Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry [J].

Ingenito, R ;

Bianchi, E ;

Fattori, D ;

Pessi, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11369-11374

[17] THE SYNTHESIS OF CYSTINE PEPTIDES BY IODINE OXIDATION OF S-TRITYL-CYSTEINE AND S-ACETAMIDOMETHYL-CYSTEINE PEPTIDES [J].

KAMBER, B ;

HARTMANN, A ;

EISLER, K ;

RINIKER, B ;

RINK, H ;

SIEBER, P ;

RITTEL, W .

HELVETICA CHIMICA ACTA, 1980, 63 (04) :899-915

[18] SAFETY CATCH PRINCIPLE IN SOLID PHASE PEPTIDE SYNTHESIS [J].

KENNER, GW ;

MCDERMOT.JR ;

SHEPPARD, RC .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (12) :636-&

[19] Total chemical synthesis of the integral membrane protein influenza A virus M2: Role of its C-terminal domain in tetramer assembly [J].

Kochendoerfer, GG ;

Salom, D ;

Lear, JD ;

Wilk-Orescan, R ;

Kent, SBH ;

DeGrado, WF .

BIOCHEMISTRY, 1999, 38 (37) :11905-11913

[20]

KOIDE T, 1993, CHEM PHARM BULL, V41, P1596

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