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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 12
BKCSDE 28(12)
December 20, 2007 

Synthesis and Conformational Study of Ser and Cys Derivatives of N-Hydroxy Diketopiperazine
Sang-woo You, Wonchoul Park, Hyoung-Tae Lee, Jeonghoon Ueom, Soonmin Jang, Kyunghee Lee, Dongyeol Lim*
N-Hydroxy diketopiperazine, Serine, Cysteine, Conformation, Glucosidase
N-Hydroxy diketopiperazine derivatives from L- and D-forms of Ser and Cys were synthesized for the first time and the ring conformation of both analogues in water was determined to be close to flat via NMR and ab initio calculations. However, the side chain of the Ser analogue was oriented toward a pseudo-equatorial position while that of the Cys analogue was slightly oriented toward a pseudo-axial direction, with a slightly distorted boat-shaped ring conformation. Among them, the D-Cys analogue was found to be a weak inhibitor of α- glucosidase.
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