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Volumn 69, Issue 12, 2004, Pages 4145-4151

Fmoc-based synthesis of peptide α-thioesters using an aryl hydrazine support

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CHEMICAL ACTIVATION; PROTEINS;

EID: 2942525475     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040140h     Document Type: Article
Times cited : (113)

References (71)
  • 49
    • 0003467672 scopus 로고
    • John Wiley & Sons: New York
    • + were used to cleave the peptidyl diazene resin, only minor amounts (<2%) of the corresponding peptide thioester were detected. A likely explanation for this result could be found in the known redox character of diazene derivatives which could lead to the oxidation of the thiol to the corresponding disulfide (see: March, J. Advanced organic chemistry. Reactions, mechanisms and structure; John Wiley & Sons: New York, 1992; pp 1205).
    • (1992) Advanced Organic Chemistry. Reactions, Mechanisms and Structure , pp. 1205
    • March, J.1
  • 51
    • 2942553864 scopus 로고    scopus 로고
    • note
    • The commercially available 4-Fmoc-hydrazinobenzoyl AM resin (Novabiochem) was used in all our experiments.
  • 53
    • 2942620977 scopus 로고    scopus 로고
    • note
    • The reactive H-AA-SEt was generated in situ from the corresponding H-AA-SEt-HCl by adding an excess of N,N-diisopropylethylamine (DIEA) during the cleavage step. Although only peptide thioesters containing either a Gly or Ala at the C-terminal positions were used in this study, it should be noted that other amino acid thioesters could also have been used with the appropriate side-chain protection when required (i.e., trifunctional amino acids). Nonetheless, it is important to note that peptide thioesters containing either an Ala or Gly residue at the C-terminus are the most commonly employed intermediates in native chemical ligation reactions (see ref 19.)
  • 54
    • 2942523878 scopus 로고    scopus 로고
    • note
    • Similar cleavage yields were obtained when propylamine was used as nucleophile to react with the peptidyl diazene resin.
  • 58
    • 2942613189 scopus 로고
    • Smith, J. A., Rivier, J. E., Eds.; Escom: Leiden
    • White, P. In Peptides, Chemistry, Structure & Biology; Smith, J. A., Rivier, J. E., Eds.; Escom: Leiden, 1992; pp 950-951.
    • (1992) Peptides, Chemistry, Structure & Biology , pp. 950-951
    • White, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.