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Volumn 36, Issue 37, 1995, Pages 6623-6626

Kemp’s triacid scaffolding for synthesis of combinatorial nonpeptide uncoded libraries

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; PSEUDOPEPTIDE; TRICARBOXYLIC ACID;

EID: 0029127055     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/00404-0399(50)1370-W     Document Type: Article
Times cited : (57)

References (12)
  • 8
    • 85024602836 scopus 로고    scopus 로고
    • Attempt to dehydrate amide diacid3 into corresponding amide anhydride4 by reflux in xylene using Dean-Stark trap under argon led to preparation of the tricyclic byproduct 7
  • 9
    • 85024609580 scopus 로고    scopus 로고
    • Mono fluorenylmethyloxycarbonylethylenediamine trifluoroacetate was prepared by acylation of mono tert. butyloxycarbonylethylenediamine with 9-fluorenyhnethyl succinimide and subsequent deprotection of Boc group.
  • 10
    • 85024602352 scopus 로고    scopus 로고
    • Formation of cyclic imides 6 have been observed
  • 11
    • 85024607246 scopus 로고    scopus 로고
    • Issakova, O., Sepetov, N., Ma, N., Kocis, P.: in preparation
  • 12
    • 85024609771 scopus 로고    scopus 로고
    • Protocol used for library synthesis: Benzotriazole-l-yl-oxy-tris(dimethylamino)-phosphoniumhexafluoro-phosphate (BOP), Hydroxybenztriazole (HOBt), DIEA (1:1:1.5) activated Boc and Fmoc amino acids were attached to βAla-Gly-βAla-Gly-O-TentaGel. After Fmoc and Boc deprotection by 50% piperidine in DMF for 10 min. and TFA/DCM (1:1), 1 hour, resp. scaffold 5 was coupled to amino acids using BOP activation in situ. The Fmoc of scaffold 5 was removed as above and carboxylic acids were coupled as symmetrical anhydrides (DIC, 30 min. preactivation) and DMAP catalysis. The Boc group of scaffold 5 was removed as above and after neutralization (DIEA) the coupling of carboxylic acids was repeated. After side chain deprotection with mixture K (82.5% TFA, 5% p-cresol, 5% thioanisol, 5% water, and 2,5% ethanedithiol) the library was washed with TFA, DCM, DMF, 0.1% aq. HCl, and 0.02% aq. HCl.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.