Peptide Synthesis with Polymer Bound Active Ester III. The Effect of Spacer Arm in Peptide Synthesis with 1-Phenyl-3-methyl-4-oximino pyrazole Resin

고분자에 결합된 활성 에스테르에 의한 펩티드합성 III. 1-페닐-3-메틸-4-옥시미노피라졸레진을 이용한 펩티드 합성에서 Spacer Arm의 효과

  • Wang, Young (Dept. of Chem. Tech., College of Eng., Seoul National University) ;
  • Lee, Yoon-Sik (Dept. of Chem. Tech., College of Eng., Seoul National University)
  • 왕영 (서울대학교 공과대학 공업화학과) ;
  • 이윤식 (서울대학교 공과대학 공업화학과)
  • Received : 1992.11.07
  • Accepted : 1993.01.18
  • Published : 1993.03.01

Abstract

Aminomethyl polystyrene resins were prepared either from chloromethyl-resin(Merrifield resin) or from direct amidoalkylation of polystyrene resin. Two kinds of aminomethlyl resin were lengthened with spacer arms via sequential coupling of five ${\varepsilon}$-aminocaproic acids(ACA) respectively. In case of the resin prepared from the Merrifield resin, the amounts of free amino group of the resin were reduced by 25~30% after each coupling of ACA. But the one from direct amidoalkylation showed 3~5% loss after each coupling of ACA. 4-Nitroso-5-aminopyrazole resin was made by reacting ACA spacer arm resin, which was made from direct amidoalkylated resin, with 5-phenyl-7-methylpyrazole [4,3-c][1,2,4]oxadiazin-3-one. Several polymeric active esters of N-blocked amino acids were prepared from the 4-nitroso-5-aminopyrazole bound resins. In anchoring step of the amino acid derivatives on the resin, no substantial effect of bulkiness was found. 4-Nitroso-5-aminopyrazole bound active ester resins were found to be very reactive in N-acylation, The resulting peptides were obtained with 90~95% yield and characterized by NMR and other physical methods.

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Acknowledgement

Supported by : 연암문화재단