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Article: Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.

TitleNoncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.
Authors
Issue Date2008
PublisherNature Publishing Group. The Journal's web site is located at http://www.natureprotocols.com/about.php
Citation
Nature Protocols, 2008, v. 3 n. 10, p. 1666-1670 How to Cite?
AbstractThis protocol describes the preparation of an N-methyl-asparagine-linked glycosyl amino acid, on the basis of a reaction between carboxylic acids and isonitriles. Under microwave/thermolysis, carboxylic acids can couple with isonitriles without an external catalyst to form N-formyl-amides, which may be further advanced to the corresponding amides, N-methyl amide and N-methyloyl amide. The example reaction of beta-galactopyranosyl isonitrile (7) with a protected aspartic acid under microwave condition in 30 min stereoselectively leads to a beta-galactopyranosyl-N-formyl-asparagine (9). Further chemical transformations readily convert 9 into beta-galactopyranosyl-N-methyl-asparagine (11).
Persistent Identifierhttp://hdl.handle.net/10722/168351
ISSN
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLi, Xen_US
dc.contributor.authorDanishefsky, SJen_US
dc.date.accessioned2012-10-08T03:17:53Z-
dc.date.available2012-10-08T03:17:53Z-
dc.date.issued2008en_US
dc.identifier.citationNature Protocols, 2008, v. 3 n. 10, p. 1666-1670en_US
dc.identifier.issn1750-2799en_US
dc.identifier.urihttp://hdl.handle.net/10722/168351-
dc.description.abstractThis protocol describes the preparation of an N-methyl-asparagine-linked glycosyl amino acid, on the basis of a reaction between carboxylic acids and isonitriles. Under microwave/thermolysis, carboxylic acids can couple with isonitriles without an external catalyst to form N-formyl-amides, which may be further advanced to the corresponding amides, N-methyl amide and N-methyloyl amide. The example reaction of beta-galactopyranosyl isonitrile (7) with a protected aspartic acid under microwave condition in 30 min stereoselectively leads to a beta-galactopyranosyl-N-formyl-asparagine (9). Further chemical transformations readily convert 9 into beta-galactopyranosyl-N-methyl-asparagine (11).en_US
dc.languageengen_US
dc.publisherNature Publishing Group. The Journal's web site is located at http://www.natureprotocols.com/about.phpen_US
dc.relation.ispartofNature protocolsen_US
dc.subject.meshAmides - Chemistryen_US
dc.subject.meshCarboxylic Acids - Chemistryen_US
dc.subject.meshHydrogen Bondingen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshNitriles - Chemistryen_US
dc.titleNoncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.en_US
dc.typeArticleen_US
dc.identifier.emailLi, X:xuechenl@hku.hken_US
dc.identifier.authorityLi, X=rp00742en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1038/nprot.2008.153en_US
dc.identifier.pmid18833204-
dc.identifier.scopuseid_2-s2.0-58149343871en_US
dc.identifier.volume3en_US
dc.identifier.issue10en_US
dc.identifier.spage1666en_US
dc.identifier.epage1670en_US
dc.identifier.isiWOS:000265781500015-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridLi, X=24168958800en_US
dc.identifier.scopusauthoridDanishefsky, SJ=7202925243en_US

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