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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 33, Number 11
BKCSDE 33(11)
November 20, 2012

Title	Synthesis of Cyclic Antifreeze Glycopeptide and Glycopeptoids and Their Ice Recrystallization Inhibition Activity
Author	Mija Ahn, Ravichandran N. Murugan, Song Yub Shin, Eunjung Kim, Jun Hyuck Lee, Hak Jun Kim, Jeong Kyu Bang
Keywords	Cyclic glycopeptide, Ice recrystallization inhibition, Solid phase synthesis, Cyclic glycopeptoid
Abstract	Until now, few groups reported the antifreeze activity of cyclic glycopeptides; however, the tedious synthetic procedure is not amenable to study the intensive structure activity relationship. A series of N-linked cyclic glycopeptoids and glycopeptide have been prepared to evaluate antifreeze activity as a function of peptide backbone cyclization and methyl stereochemical effect on the rigid Thr position. This study has combined the cyclization protocol with solid phase peptide synthesis and obtained significant quantities of homogeneous cyclic glycopeptide and glycopeptoids. Analysis of antifreeze activity revealed that our cyclic peptide demonstrated RI activity while cyclic glycopeptoids showed no RI activity. These results suggest that the subtle changes in conformation and Thr orientation dramatically influence RI activity of N-linked glycopeptoids
Page	3565 - 3570
Full Text	PDF

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