Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis

被引：34

作者：

Hu, BH ^{[1
]}

Messersmith, PB ^{[1
]}

机构：

[1] Northwestern Univ, Dept Biomed Engn, Evanston, IL 60208 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 31期

基金：

美国国家卫生研究院;

关键词：

biologically active compounds; amino acids and derivatives; solid-phase synthesis; peptides and polypeptides;

D O I：

10.1016/S0040-4039(00)00957-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic ethyl orthoformate (Ceof) was utilized as a protecting group to protect the catechol hydroxyl groups of 3,4-dihydroxyphenylalanine (DOPA). This protecting group is stable to strong bases and nucleophiles, and can be removed efficiently by 1 M trimethylsilyl bromide in trifluoroacetic acid in the presence of scavengers at 0 degrees C for 60 min. FmocDOPA(Ceof)-OH was synthesized in high yield and applied along with other Fmoc-amino acids to the solid-phase peptide synthesis of a DOPA-containing decapeptide from a mussel adhesive protein. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5795 / 5798

页数：4

共 18 条

[1] 9-FLUORENYLMETHOXYCARBONYL FUNCTION, A NEW BASE-SENSITIVE AMINO-PROTECTING GROUP [J].

CARPINO, LA ;

HAN, GY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) :5748-&

[2] TRIFLUOROACETYLATION OF AMINO-ACIDS AND PEPTIDES BY ETHYL TRIFLUOROACETATE [J].

CURPHEY, TJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2805-2807

[3] TOTAL SYNTHESIS OF (+/-)-PANCRATISTATIN [J].

DANISHEFSKY, S ;

LEE, JY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4829-4837

[4]

DIETL F, 1985, SYNTHESIS-STUTTGART, P626

[5] SOLID-PHASE PEPTIDE-SYNTHESIS UTILIZING 9-FLUORENYLMETHOXYCARBONYL AMINO-ACIDS [J].

FIELDS, GB ;

NOBLE, RL .

INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1990, 35 (03) :161-214

[6] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .67. A GENERAL-SYNTHESIS OF DERIVATIVES OF OPTICALLY PURE 2-(1-AMINOALKYL)THIAZOLE-4-CARBOXYLIC ACIDS [J].

HAMADA, Y ;

SHIBATA, M ;

SUGIURA, T ;

KATO, S ;

SHIOIRI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1252-1255

[7] METHODOLOGICAL IMPLICATIONS OF SIMULTANEOUS SOLID-PHASE PEPTIDE-SYNTHESIS .1. COMPARISON OF DIFFERENT COUPLING PROCEDURES [J].

HUDSON, D .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :617-624

[8] SYNTHESIS OF N-2,2,2-(TRICHLOROETHOXYCARBONYL)-L-AMINO ACIDS AND N-(9-FLUORENYLMETHOXYCARBONYL)-L-AMINO ACIDS INVOLVING SUCCINIMIDOXY ANION AS A LEAVING GROUP IN AMINO-ACID PROTECTION [J].

LAPATSANIS, L ;

MILIAS, G ;

FROUSSIOS, K ;

KOLOVOS, M .

SYNTHESIS-STUTTGART, 1983, (08) :671-673

[9]

LAURSEN RA, 1992, STRUCTURE CELLULAR S, P55

[10] DISTRIBUTION OF L-DOPA AND RELATED AMINO-ACIDS IN-VICIA [J].

LONGO, R ;

CASTELLA.A ;

SBERZE, P ;

TIBOLLA, M .

PHYTOCHEMISTRY, 1974, 13 (01) :167-171

← 1 2 →