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- Publisher Website: 10.1038/nprot.2008.153
- Scopus: eid_2-s2.0-58149343871
- PMID: 18833204
- WOS: WOS:000265781500015
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Article: Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.
Title | Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages. |
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Authors | |
Issue Date | 2008 |
Publisher | Nature 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? |
Abstract | This 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 Identifier | http://hdl.handle.net/10722/168351 |
ISSN | 2023 Impact Factor: 13.1 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Li, X | en_US |
dc.contributor.author | Danishefsky, SJ | en_US |
dc.date.accessioned | 2012-10-08T03:17:53Z | - |
dc.date.available | 2012-10-08T03:17:53Z | - |
dc.date.issued | 2008 | en_US |
dc.identifier.citation | Nature Protocols, 2008, v. 3 n. 10, p. 1666-1670 | en_US |
dc.identifier.issn | 1750-2799 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/168351 | - |
dc.description.abstract | This 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.language | eng | en_US |
dc.publisher | Nature Publishing Group. The Journal's web site is located at http://www.natureprotocols.com/about.php | en_US |
dc.relation.ispartof | Nature protocols | en_US |
dc.subject.mesh | Amides - Chemistry | en_US |
dc.subject.mesh | Carboxylic Acids - Chemistry | en_US |
dc.subject.mesh | Hydrogen Bonding | en_US |
dc.subject.mesh | Molecular Structure | en_US |
dc.subject.mesh | Nitriles - Chemistry | en_US |
dc.title | Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages. | en_US |
dc.type | Article | en_US |
dc.identifier.email | Li, X:xuechenl@hku.hk | en_US |
dc.identifier.authority | Li, X=rp00742 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1038/nprot.2008.153 | en_US |
dc.identifier.pmid | 18833204 | - |
dc.identifier.scopus | eid_2-s2.0-58149343871 | en_US |
dc.identifier.volume | 3 | en_US |
dc.identifier.issue | 10 | en_US |
dc.identifier.spage | 1666 | en_US |
dc.identifier.epage | 1670 | en_US |
dc.identifier.isi | WOS:000265781500015 | - |
dc.publisher.place | United Kingdom | en_US |
dc.identifier.scopusauthorid | Li, X=24168958800 | en_US |
dc.identifier.scopusauthorid | Danishefsky, SJ=7202925243 | en_US |
dc.identifier.issnl | 1750-2799 | - |