Peptide synthesis. I. The use of p-toluenesulfonyl chloride for carboxyl activation

Theodoropoulos, D; Gazopoulos, J

dc.contributor.author	Theodoropoulos, D	en
dc.contributor.author	Gazopoulos, J	en
dc.date.accessioned	2014-03-01T01:37:39Z
dc.date.available	2014-03-01T01:37:39Z
dc.date.issued	1962	en
dc.identifier.issn	00223263	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/21587
dc.relation.uri	http://www.scopus.com/inward/record.url?eid=2-s2.0-0000940054&partnerID=40&md5=4c06dac20c9546efe3b8b001da91d0ef	en
dc.title	Peptide synthesis. I. The use of p-toluenesulfonyl chloride for carboxyl activation	en
heal.type	journalArticle	en
heal.publicationDate	1962	en
heal.abstract	p-Toluenesulfonyl chloride (tosyl chloride) has been used for the carboxyl activation of carbobenzoxy amino acids and peptides via the formation of mixed p-toluenesulfonic-carboxylic anhydrides. Although carbobenzoxy L-amino acids, thus activated, do not racemize when condensed with amino acid and peptide esters, carbobenzoxyglycyl-L-phenylalanine, on the other hand, gives completely racemic carbobenzoxyglycyl-D,L-phenylalanylglycine ethyl ester, when coupled with glycine ethyl ester in tetrahydrofuran or acetonitrile as the solvent. The thionyl chloride method for carboxyl activation also resulted in extensive racemization.	en
heal.journalName	Journal of Organic Chemistry	en
dc.identifier.volume	27	en
dc.identifier.issue	6	en
dc.identifier.spage	2091	en
dc.identifier.epage	2093	en