Removal of acyl protective groups from glycopeptides: Base does not epimerize peptide stereocenters, and β-elimination is slow

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 560-565

  Sjölin, Petter ^a   Elofsson, Mikael ^a   Kihlberg, Jan ^a  

^a LUND INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030040734     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951817r     Document Type: Article

References (28)

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27. Within a project dealing with the T cell response to neoglycopeptides (ef. ref 13), the decapeptide DYGISQINSR carrying per-Ο-benzoylated lactose at the central serine was prepared. Debenzoylation of this glycopeptide was accompanied by extensive β-elimination (∼75%), but the deprotected glycopeptide and the product of β-elimination had significantly different retention times on reversed-phase HPLC (14.0 and 16.2 min, respectively, when analyzed as described in the Experimental Section). Sjölin, P.; Kihlberg, J. Unpublished results.
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