THE FACILE SYNTHESIS OF ALA-GLU-TYR(P)-SER-ALA BY GLOBAL DI-TERT-BUTYL N,N-DIETHYLPHOSPHORAMIDITE PHOSPHITE-TRIESTER PHOSPHORYLATION OF A RESIN-BOUND PEPTIDE

被引：28

作者：

PERICH, JW ^{[1
]}

NGUYEN, DL ^{[1
]}

REYNOLDS, EC ^{[1
]}

机构：

[1] UNIV MELBOURNE,SCH DENT SCI,BIOCHEM & MOLEC BIOL UNIT,MELBOURNE,VIC 3000,AUSTRALIA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 32期

关键词：

SOLID-PHASE SYNTHESIS; HBTU; PHOSPHORYLATION; DI-T-BUTYL N; N-DIETHYLPHOSPHORAMIDITE; TYR(P)-CONTAINING PEPTIDE;

D O I：

10.1016/0040-4039(91)80620-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The O-phosphotyrosyl-containing peptide, Ala-Glu-Tyr(P)-Ser-Ala, was prepared by a methodology which featured 'phosphite-triester' phosphorylation of a resin-bound Tyr-containing peptide. The peptide-resin was assembled by Fmoc/solid-phase peptide synthesis using HBTU as the coupling reagent and the tyrosyl residue incorporated as Fmoc-Tyr-OH. The peptide-resin was phosphorylated using di-t-butyl N,N-diethylphosphoramidite/1H-tetrazole followed by m-chloroperoxybenzoic acid oxidation. Simultaneous peptide-resin cleavage and peptide deprotection was effected by 5% anisole/TFA to give the crude Tyr(P)-peptide in high yield and in > 95% purity.

引用

页码：4033 / 4034

页数：2

共 8 条

[1] AUTOMATIC SYNTHESIS OF PHOSPHOPEPTIDES BY PHOSPHORYLATION ON THE SOLID-PHASE [J].

DEBONT, HBA ;

VANBOOM, JH ;

LISKAMP, RMJ .

TETRAHEDRON LETTERS, 1990, 31 (17) :2497-2500

[2] PROTEIN-TYROSINE KINASES [J].

HUNTER, T ;

COOPER, JA .

ANNUAL REVIEW OF BIOCHEMISTRY, 1985, 54 :897-930

[3] SYNTHESIS OF O-PHOSPHOTYROSINE-CONTAINING PEPTIDES .3. SYNTHESIS OF H-PRO-TRY(P)-VAL-OH VIA DIMETHYL-PHOSPHATE PROTECTION AND THE USE OF IMPROVED DEPROTECTION PROCEDURES [J].

KITAS, EA ;

PERICH, JW ;

TREGEAR, GW ;

JOHNS, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4181-4187

[4] DI-TERT-BUTYL N,N-DIETHYLPHOSPHORAMIDITE AND DIBENZYL N,N-DIETHYLPHOSPHORAMIDITE - HIGHLY REACTIVE REAGENTS FOR THE PHOSPHITE-TRIESTER PHOSPHORYLATION OF SERINE-CONTAINING PEPTIDES [J].

PERICH, JW ;

JOHNS, RB .

TETRAHEDRON LETTERS, 1988, 29 (19) :2369-2372

[5]

PERICH JW, 1990, BIOCHEM BIOPH RES CO, V170, P635

[6]

PERICH JW, 1991, IN PRESS AUST J CHEM

[7]

VALERIO RM, 1989, INT J PEPT PROT RES, V33, P428

[8] SYNTHESIS OF O-PHOSPHOTYROSINE-CONTAINING PEPTIDES .2. SOLUTION-PHASE SYNTHESIS OF ASN-GLU-PTYR-THR-ALA THROUGH METHYL PHOSPHATE PROTECTION [J].

VALERIO, RM ;

PERICH, JW ;

KITAS, EA ;

ALEWOOD, PF ;

JOHNS, RB .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (09) :1519-1525

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