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Volumn 74, Issue 19, 2009, Pages 7383-7388

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; HIGH YIELD; POLYSTYRENE RESINS; SIDE-CHAIN; SOLID PHASE SYNTHESIS; THIOACIDS; THIOESTERS;

EID: 70349473080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901218g     Document Type: Article
Times cited : (16)

References (81)
  • 56
    • 0035078547 scopus 로고    scopus 로고
    • The use of allyl esters in alloxycarbamates as a protecting group system orthogonal with both Boc and Fmoc chemistries is widely established. (a)
    • The use of allyl esters in alloxycarbamates as a protecting group system orthogonal with both Boc and Fmoc chemistries is widely established. (a) Grieco, P.; Gitu, P. M.; Hruby, V. J. J. Peptide. Res. 2001, 57, 250-256.
    • (2001) J. Peptide. Res. , vol.57 , pp. 250-256
    • Grieco, P.1    Gitu, P.M.2    Hruby, V.J.3
  • 59
    • 0027282913 scopus 로고
    • Alternative possibilities include the nitrobenzenesulfonyl protecting group for amines
    • (d) Bloomberg, G. B.; Askin, D.; Gargaro, A. R.; Tanner, M. A. J. Tetrahedron Lett. 1993, 34, 4709-4712. Alternative possibilities include the nitrobenzenesulfonyl protecting group for amines.
    • (1993) J. Tetrahedron Lett. , vol.34 , pp. 4709-4712
    • Bloomberg, G.B.1    Askin, D.2    Gargaro, A.R.3    Tanner, M.A.4
  • 71
    • 70349438103 scopus 로고    scopus 로고
    • note
    • The peptides were isolated in the form of their N-Boc derivatives simply owing to the use of Boc-protected building blocks. Use of Fmocprotected builing blocks in the final coupling step will necessarily yield peptides with the N-terminus unprotected.
  • 75
    • 70349471878 scopus 로고    scopus 로고
    • note
    • This is evident simply from the yields of the isolated thioacids 25 and 27, which require average minimum coupling yields of >93% and >97%, respectively, for each coupling deprotection cycle. For comparable reasons premature peptide cleavage by diketopiperazine formation at the level of deprotection of the dipeptide and the migration of side-chain protecting groups to N-terminal amines on neutralization do not appear to be major concerns, at least for the examples provided.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.