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Volumn 10, Issue 4, 2004, Pages 875-887

Efficient Synthesis of S-linked Glycopeptides in Aqueous Solution by a Convergent Strategy

Author keywords

Carbohydrates glycopeptides; Substitution; Thioglycosides

Indexed keywords

AMINO ACIDS; HALOGENATION; SYNTHESIS (CHEMICAL);

EID: 1542349356     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305163     Document Type: Article
Times cited : (75)

References (73)
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    • note
    • This procedure is a significant advance in the convergent assembly of S-linked glycopeptides since there have not been any reports on direct S-glycosylation prior to this work. An advantage of this procedure is the ready availability of peptides that contain cysteine or homocysteine. For instance, through native chemical ligation techniques, see: ref. [9].
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    • Besides ref. [10] and [11], for the synthesis of a-S-linked glycosyl amino acids, see: a) L. Käsbeck, H. Kessler, Liebigs Ann./Recl. 1997, 165-167;
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    • note
    • Compound 33 and 46 are considered to mimic native N-linked glycopeptides based on the viewpoint that the distance between the sugar and the peptide backbone in 33 and 46 is similar to the N-glycan linkage in asparagines.
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    • note
    • It is worth mentioning that α-thioglycosides 37, 39, and 40 mimic the important Tn antigen structure.
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    • note
    • β-S-Linked glycopeptides can also be prepared by our previous procedure, see ref. [9].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.