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Titolo:
MECHANISM OF AMIDE FORMATION BY CARBODIIMIDE FOR BIOCONJUGATION IN AQUEOUS-MEDIA
Autore:
NAKAJIMA N; IKADA Y;
Indirizzi:
KYOTO UNIV,BIOMED ENGN RES CTR,SAKYO KU,53 KAWAHARA CHO KYOTO 606 JAPAN KYOTO UNIV,BIOMED ENGN RES CTR,SAKYO KU KYOTO 606 JAPAN
Titolo Testata:
Bioconjugate chemistry
fascicolo: 1, volume: 6, anno: 1995,
pagine: 123 - 130
SICI:
1043-1802(1995)6:1<123:MOAFBC>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
WATER-SOLUBLE CARBODIIMIDES; F1 ADENOSINE-TRIPHOSPHATASE; CROSS-LINKING; CHEMICAL-REACTIONS; ESCHERICHIA-COLI; HEAVY-MEROMYOSIN; ALPHA-SUBUNITS; CARBOXYL GROUP; CROSSLINKING; HEADS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
34
Recensione:
Indirizzi per estratti:
Citazione:
N. Nakajima e Y. Ikada, "MECHANISM OF AMIDE FORMATION BY CARBODIIMIDE FOR BIOCONJUGATION IN AQUEOUS-MEDIA", Bioconjugate chemistry, 6(1), 1995, pp. 123-130

Abstract

To study the mechanism of amide formation between carboxylic acid andamine in aqueous media using 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (EDC), hydrogels with two different types of carboxyl group locations were employed as substrates containing the carboxylic acid, while ethylenediamine and benzylamine were used as amine. In parallel, a study was undertaken with cyclizable carboxylic acids (maleic acid and poly(acrylic acid) and noncyclizable carboxylic acids (fumaric acid and poly(ethylene glycol) with the terminal carboxyl groups) to assess the reaction products by C-13-NMR and IR. EDC rapidly lost its activity in aqueous media of low pH, producing the corresponding urea derivative, but was very stable at neutral and higher pH regions. EDC could react with carboxyl groups at a relatively narrow low pHrange such as 3.5-4.5. If carboxyl groups were cyclizable, they wouldreact quickly with EDC producing carboxylic anhydrides, which formed the corresponding amides when amine compounds were present. On the other hand, a trace of amide was formed in the case of noncyclizable carboxylic acids. In addition, an excess of EDC caused an undesired side reaction to form stable N-acylurea, regardless of the special location of carboxylic acids.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/10/20 alle ore 14:39:19