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Volumn 52, Issue 1, 2011, Pages 17-20

Neoglycopeptides through direct functionalization of cysteine

Author keywords

Azido sugars; Chemical ligation; Cysteine; Neoglycopeptide

Indexed keywords

CYSTEINE; GLUCOPYRANOSIDE; GLYCOPEPTIDE; PEPTIDE DERIVATIVE; PYRANOSIDE; TRIAZOLE DERIVATIVE;

EID: 78649846526     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.021     Document Type: Article
Times cited : (20)

References (53)
  • 4
    • 34547908618 scopus 로고    scopus 로고
    • Synthesis and Application of Glycopeptide and Glycoprotein Mimetics
    • D. Specker, and V. Wittmann Synthesis and Application of Glycopeptide and Glycoprotein Mimetics Topics in Current Chemistry 267 2007 65 107
    • (2007) Topics in Current Chemistry , vol.267 , pp. 65-107
    • Specker, D.1    Wittmann, V.2
  • 32
    • 61649119302 scopus 로고    scopus 로고
    • For recent references on glycoconjugate constructions using click cycloaddition see: X. Zhang, X. Yang, and S. Zhang Synth. Commun. 39 2009 830 844
    • (2009) Synth. Commun. , vol.39 , pp. 830-844
    • Zhang, X.1    Yang, X.2    Zhang, S.3
  • 45
    • 78649845977 scopus 로고    scopus 로고
    • note
    • +.
  • 46
    • 78649888240 scopus 로고    scopus 로고
    • note
    • General procedure for S-propargyl peptides and free sugars adduct formation: To a solution of crude S-propargyl derivative (0.2 mmol), of the azido sugar (0.2 mmol) and sodium ascorbate (8 mg, 0.04 mmol) in water (4 ml) was added, at room temperature a solution of copper(II) acetate (4 mg, 0.02 mmol) in water (0.5 ml). The solution turned immediately pale green. The reaction was stopped when the intense blue color reappeared. Chelex resin (500 mg) was then added to the blue solution and the suspension was stirred until the solution became colorless. The resin was filtered off and the resulting solution was freeze-dried. Purification was achieved by LH20 gel filtration. Elution with water provided pure triazole.
  • 47
    • 78649897816 scopus 로고    scopus 로고
    • note
    • It must be noted that the 1,4 triazole is the major product but is often contaminated by less than 10% of another yet unknown compound which is not 1,5 triazole as seen from proton and carbon NMR spectra. The structure of the latter was also established on the basis of carbon NMR (see Ref. 10h)
  • 48
    • 78649857833 scopus 로고    scopus 로고
    • note
    • 2- 296.0905, found: 296.0920.
  • 53
    • 78649874070 scopus 로고    scopus 로고
    • note
    • - 737.2688, found: 737.2710.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.