Solid-phase peptide synthesis using Nα-trityl-amino acids

被引:11
作者
de la Torre, BG
Marcos, MA
Eritja, R
Albericio, F
机构
[1] CSIC, Inst Mol Biol, Dept Mol Genet, E-08034 Barcelona, Spain
[2] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
来源
LETTERS IN PEPTIDE SCIENCE | 2001年 / 8卷 / 06期
关键词
amino acid derivatives; amino protection; N-trityl-amino acids; protecting group; solid phase peptide synthesis;
D O I
10.1023/A:1016247817737
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The preparation of N-alpha-trityl-amino acids is described. Several derivatives of trifunctional amino acids carrying acid- and base-labile side-chain protecting groups and the trityl group at the N-alpha position are prepared for first time. The incorporation of N-alpha-trityl-amino acids into peptide sequences using solid-phase protocols was achieved. The use of the trityl group for the protection of the alpha-amino group in conjunction with base-labile side-chain protecting groups constitutes a new method for the assembly of peptides in mild conditions.
引用
收藏
页码:331 / 338
页数:8
相关论文
共 15 条
[1]   PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].
ALBERICIO, F ;
KNEIBCORDONIER, N ;
BIANCALANA, S ;
GERA, L ;
MASADA, RI ;
HUDSON, D ;
BARANY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3730-3743
[2]   NPE-RESIN, A NEW APPROACH TO THE SOLID-PHASE SYNTHESIS OF PROTECTED PEPTIDES AND OLIGONUCLEOTIDES .2. SYNTHESIS OF PROTECTED PEPTIDES [J].
ALBERICIO, F ;
GIRALT, E ;
ERITJA, R .
TETRAHEDRON LETTERS, 1991, 32 (11) :1515-1518
[3]   Use of N-tritylamino acids and PyAOP(1) for the suppression of diketopiperazine formation in Fmoc/(t)Bu solid-phase peptide synthesis using alkoxybenzyl ester anchoring linkages [J].
Alsina, J ;
Giralt, E ;
Albericio, F .
TETRAHEDRON LETTERS, 1996, 37 (24) :4195-4198
[4]  
BARLOS K, 1986, LIEBIGS ANN CHEM, P1950
[5]   EFFICIENT ONE-POT SYNTHESIS OF N-TRITYL AMINO-ACIDS [J].
BARLOS, K ;
PAPAIOANNOU, D ;
THEODOROPOULOS, D .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1324-1326
[6]  
BARLOS K, 1984, INT J PEPT PROT RES, V23, P300
[7]  
BARLOS K, 1987, LIEBIGS ANN CHEM, P1025
[8]  
BODANSZKY M, 1982, INT J PEPT PROT RES, V20, P387
[9]   Synthesis and binding properties of oligonucleotides carrying nuclear localization sequences [J].
de la Torre, BG ;
Albericio, F ;
Saison-Behmoaras, E ;
Bachi, A ;
Eritja, R .
BIOCONJUGATE CHEMISTRY, 1999, 10 (06) :1005-1012
[10]   SYNTHETIC METHODS AND REACTIONS .29. CLEAVAGE OF ESTERS AND ETHERS WITH IODOTRIMETHYLSILANE [J].
HO, TL ;
OLAH, GA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (12) :774-775