Synthesis of a modified carboxylate-binding pocket of vancomycin

A 16-membered tetrapeptide macrocycle I, an analog of the vancomycin binding pocket, has been designed and synthesized using the efficient macrocyclization of the corresponding linear tetrapeptide via biaryl ether formation. In acetone, I adopted a right conformation needed for binding carboxylate anion even in the absence of -Ac-D-Ala-D-Ala-OH. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 36, 27, 4781-4
Year:
1995
Keywords:
Note:
CAN 123:314492
34-3
Amino Acids, Peptides, and Proteins
Inst. Chim. Subst. Nat.,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
1404-90-6DP (Vancomycin); 169825-19-8P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (synthesis of a modified carboxylate binding pocket of vancomycin); 20274-69-5; 78342-42-4; 89536-84-5; 90508-28-4 (N-Allyloxycarbonylalanine); 169825-23-4 Role: RCT (Reactant), RACT (Reactant or reagent) (synthesis of a modified carboxylate binding pocket of vancomycin); 167423-69-0P; 169825-20-1P; 169825-21-2P; 169825-22-3P; 169825-24-5P; 169825-25-6P; 169825-26-7P; 169825-27-8P; 169825-28-9P; 169825-29-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (synthesis of a modified carboxylate binding pocket of vancomycin)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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