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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 42, Number 2
JKCSEZ 42(2)
April 20, 1998 

 
Title
Synthsis of Dynorphin B Analogues by Solid-Phase Method

고상법에 의한 Dynorphin B 유도체의 합성
Author
Soon Uoong Kook, Ki Nam Son*

국순웅,손기남
Keywords
Abstract
Dynorphin B유도체들인 [Arg11, D-Ala12] dynorphin B및, [D-Ala2, Ala6, Arg11, D-Ala12] dynorphin B, and dynorphin B (1-11)를 고상법으로 합성하였다.에탄올 용액에서 2%의 디비닐벤젠으로 교차결합된 파라-염화메틸폴리스티렌 수지와 Thr을 반응시켜 수지 1g당 1.20 mmol의 Thr을 치환시켰다. 모든 아미노산의 아미노기는 t-Boc기로 보호하였으며 Tyr와Arg의 곁사슬은 2,6-디클로로벤질기와 니트로기로 각각 보호하였다. 각 유도체는 DCC와HOBT를 짝지음 시약으로 사용하여 단계적 합성법으로 합성하였으며 생성물은 MeOH/MeCN (3/1)을 전개용매로 하여 Sephadex LH-20 column (2×50 cm)으로 정제하였으며 HPLC와 아미노산 분석기로 확인하였다.

Dynorphin B analogues, [Arg11, D-Ala12] dynorphin B, [D-Ala2, Ala6, Arg11, D-Ala12] dynorphin B, and dynorphin B (1-11) were synthesized by solid-phase method. A chloromethylated polystyrene resin cross-linked with 2% divinylbenzene was substituted with Thr in ethanol to contain 1.20 mmol Thr/g of resin. All amino groups of amino acids were protected with t-Boc group and 2,6-dichlorobenzyl and nitro groups were used to protect the side chains of Tyr and Arg, respectively. Stepwise synthetic method was applied for synthesis of the products. Dicyclohexylcarbodiimide (DCC) and 1-hydroxybenzotriazole (HOBT) were used as the coupling reagents. The crude peptides were purified by gel filteration on Sephadex LH-20 column (2×50 cm) using MeOH/MeCN (3/1) and then characterized with HPLC, amino acid analyzer.

Page
214 - 219
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