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

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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 http://hdl.handle.net/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

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