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Fluorenylmethoxycarbonyl-protected O-Glycosyl-N-methyl amino acids: Building blocks for the synthesis of conformationally tuned glycopeptide antigens

 
: Buba, Annette E.; Löwe, Holger; Kunz, Horst

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European Journal of Organic Chemistry (2015), No.26, pp.5764-5774
ISSN: 1434-193X
ISSN: 1099-0690
English
Journal Article
Fraunhofer ICT-IMM ()
solid-phase synthesis; glycopeptides; Amino acids; Antigens

Abstract
Peptide antibiotics often contain N-methylated amino acids. These N-methylamino components enhance the metabolic stability and strongly influence the conformational behavior of these peptide drugs. N-Methyl-O-glycosyl amino acids, in particular, threonine and serine derivatives, are unknown so far. Fmoc-protected N-methyl-O-glycosyl-threonine and -serine building blocks, including sialyl TN antigens, have been synthesized for the first time by converting the Fmoc-protected O-glycosyl amino acids or their tert-butyl esters into the corresponding oxazolidinones followed by reductive ring-opening. These new components are considered interesting for the construction of modified mucin glycopeptide anti-tumor vaccines with extended biological half-life.

: http://publica.fraunhofer.de/documents/N-360304.html