title: Amide and Peptide Bond Formation in Water at Room Temperature.
abstract: A general and environmentally responsible method for the formation of amide/peptide bonds in an aqueous micellar medium is described. Use of uronium salt (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) as a coupling reagent, 2,6-lutidine, and TPGS-750-M represents mild conditions associated with these valuable types of couplings. The aqueous reaction medium is recyclable leading to low E Factors.
authors.affiliation: †Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Gabriel
authors.affiliation: †Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Megan
authors.initials: M
authors.lastname: Keener
authors.affiliation: ‡Novartis Pharma AG, Basel, Switzerland.
authors.forename: Fabrice
authors.initials: F
authors.lastname: Gallou
authors.affiliation: †Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Bruce H
authors.initials: BH
authors.lastname: Lipshutz
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry; D013696:Temperature; D014867:Water / Q000737:chemistry*
chemical_list: C000593117:1-((1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylaminomorpholinomethylene))methanaminium; D000577:Amides; D007097:Imines; D007202:Indicators and Reagents; D009025:Morpholines; D010455:Peptides; D011725:Pyridines; D013501:Surface-Active Agents; D014867:Water; C013093:2,6-lutidine