CARBOXYMETHYL-SUBSTITUTED BIFUNCTIONAL CHELATORS - PREPARATION OF ARYL ISOTHIOCYANATE DERIVATIVES OF 3-(CARBOXYMETHYL)-3-AZAPENTANEDIOIC ACID, 3,12-BIS(CARBOXYMETHYL)-6,9-DIOXA-3,12-DIAZATETRADECANEDIOIC ACID, AND 1,4,7,10-TETRAAZACYCLODODECANE-N,N',N'',N'''-TETRAACETIC ACID FOR USE AS PROTEIN LABELS

被引：35

作者：

KLINE, SJ ^{[1
]}

BETEBENNER, DA ^{[1
]}

JOHNSON, DK ^{[1
]}

机构：

[1] ABBOTT LAB,DEPT 90M,ABBOTT PK,IL 60064

来源：

BIOCONJUGATE CHEMISTRY | 1991年 / 2卷 / 01期

关键词：

D O I：

10.1021/bc00007a005

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

3-(Carboxymethyl)-3-azapentanedioic acid (NTA), 3,12-bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecanedioic acid (EGTA), and 1,4,7,10-tetraazacyclododecane-N,N',N",N"'-tetraacetic acid (DOTA) structures having a 4-nitrophenyl substituent attached via an alkyl spacer to the methylene carbon atom of one carboxymethyl arm of the chelator were obtained by alkylation of 4-nitrophenylalanine with bromoacetic acid (NTA), by reductive alkylation of 1,8-diamino-3,6-dioxaoctane with (4-nitrophenyl)pyruvic acid followed by alkylation with bromoacetic acid (EGTA), and by alkylation of the trimethyl ester of 1,4,7,10-tetraazacyclododecane-N,N',N"-triacetic acid with the methyl ester of alpha-bromo-4-(4-nitrophenyl)pentanoic acid and subsequent saponification (DOTA). The nitrophenyl-substituted chelators were converted to the corresponding amines by hydrogenation then reacted with thiophosgene to give the protein-reactive aryl isothiocyanate derivatives.

引用

页码：26 / 31

页数：6

共 23 条

[1] BIFUNCTIONAL CHELATING-AGENTS .1. 1-(PARA-AMINOPHENETHYL)-ETHYLENEDIAMINETETRA-ACETIC ACID [J].