Journal
NATURE PROTOCOLS
Volume 3, Issue 10, Pages 1666-1670Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/nprot.2008.153
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Funding
- National Institutes of Health [CA28824]
- NATIONAL CANCER INSTITUTE [R01CA028824, R37CA028824] Funding Source: NIH RePORTER
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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).
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