title: An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin.
abstract: Herein we report a direct and efficient method for the synthesis of four new carboxylate-isostere analogs of daptomycin. The side chain carboxylic acid moieties of the aspartic acids (Asp-3, Asp-7 and Asp-9) and β-methyl glutamic acid (MeGlu-12) were all converted into the corresponding carboxylate isosteres using direct synthetic procedures. The present study also describes an esterification protocol to overcome the possible backbone cyclization of the activated side chain carboxylic acid group of either Asp or Glu onto the backbone amide.
authors.affiliation: Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, USA.
authors.forename: Sabesan
authors.initials: S
authors.lastname: Yoganathan
authors.forename: Ning
authors.initials: N
authors.lastname: Yin
authors.forename: Yong
authors.initials: Y
authors.lastname: He
authors.forename: Michael F
authors.initials: MF
authors.lastname: Mesleh
authors.forename: Yu Gui
authors.initials: YG
authors.lastname: Gu
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
mesh_terms: D001224:Aspartic Acid / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D017576:Daptomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D018698:Glutamic Acid / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D001224:Aspartic Acid; D018698:Glutamic Acid; D017576:Daptomycin