New chemistry with old functional groups: on the reaction of isonitriles with carboxylic acids--a route to various amide types.
Thermolysis of isonitriles with carboxylic acids provides, in one step, N-formyl imides (see, for example, 8 + 19 --> 21). The resultant N-formyl group can be converted to N-H, NCH2OH, or NCH3. This chemistry allows for a new route for synthesizing beta-N (asparagine)-linked glycosyl amino acids.
Li
Xuechen
X
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.
Danishefsky
Samuel J
SJ
D000577:Amides / Q000138:chemical synthesis*; D001216:Asparagine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D007094:Imides / Q000737:chemistry; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry*
D000577:Amides; D002264:Carboxylic Acids; D006020:Glycopeptides; D007094:Imides; D009570:Nitriles; D001216:Asparagine