A convenient and scaleable procedure for removing the Fmoc group in solution

被引:68
作者
Sheppeck, JE [1 ]
Kar, H [1 ]
Hong, H [1 ]
机构
[1] ChemRx Adv Technol, S San Francisco, CA 94080 USA
关键词
protecting groups; thiols; polymer support; supported reagents/reaction;
D O I
10.1016/S0040-4039(00)00853-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved and simple reagent system was developed to facilitate solution-phase deprotection of Fmoc-protected amines. Catalytic DBU in the presence of an aliphatic or polymer-supported thiol rapidly removed the Fmoc group to provide the amine free base in excellent yields and purity on multi-gram scale. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5329 / 5333
页数:5
相关论文
共 19 条
[1]  
Alves LC, 1996, PEPTIDE RES, V9, P92
[2]  
Bayermann M., 1990, J ORG CHEM, V55, P721
[3]   A general procedure of the peptide synthesis. [J].
Bergmann, M ;
Zervas, L .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1932, 65 (07) :1192-1201
[4]   Polymer-supported quenching reagents for parallel purification [J].
Booth, RJ ;
Hodges, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4882-4886
[5]   9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP [J].
CARPINO, LA ;
HAN, GY .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3404-&
[7]   POLYSTYRENE-BASED DEBLOCKING-SCAVENGING AGENTS FOR THE 9-FLUORENYLMETHYLOXYCARBONYL AMINO-PROTECTING GROUP [J].
CARPINO, LA ;
MANSOUR, EME ;
CHENG, CH ;
WILLIAMS, JR ;
MACDONALD, R ;
KNAPCZYK, J ;
CARMAN, M ;
LOPUSINSKI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (05) :661-665
[8]   TRIS(2-AMINOETHYL)AMINE AS A SUBSTITUTE FOR 4-(AMINOMETHYL)PIPERIDINE IN THE FMOC/POLYAMINE APPROACH TO RAPID PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
SADATAALAEE, D ;
BEYERMANN, M .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1673-1675
[9]   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-&
[10]  
CHANG CD, 1980, INT J PEPT PROT RES, V15, P59