Detection and control of aspartimide formation in the synthesis of cyclic peptides.
Extensive two-dimensional NMR analysis was employed to characterize the structural identity of the macrocyclic peptide lactam and the imide analog, a major side reaction product when allyl ester was used to protect the side chain of aspartic acid. A straightforward protocol modification was developed to minimize aspartimide formation during the synthesis of cyclic peptides.
Flora
David
D
Lilly Research Laboratories, A Division of Eli Lilly & Company, Lilly Corporate Center, Indianapolis, IN 46285, USA.
Mo
Huaping
H
Mayer
John P
JP
Khan
M Amin
MA
Yan
Liang Z
LZ
D001224:Aspartic Acid / Q000031:analogs & derivatives*; D020650:Combinatorial Chemistry Techniques; D007769:Lactams; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000302:isolation & purification; D011786:Quality Control
D007769:Lactams; D010456:Peptides, Cyclic; D001224:Aspartic Acid; C075871:aspartimide