Silyl protection in the solid-phase synthesis of N-linked glycopeptides. Preparation of glycosylated fluorogenic substrates for subtilisins.
The trimethylsilyl (TMS) group was used for protection of the hydroxy groups of three disaccharide 1-amino-alditols and of the glycosylamines of glucose, maltotriose and maltoheptose. The per-O-trimethylsilylated derivatives were coupled with N alpha-Fmoc-Asp(Cl)-OPfp 7 to give six glycosylated building blocks for the solid-phase synthesis of N-linked glycopeptides. Building block 8 was used in the synthesis of five internally quenched fluorescent substrates which were studied by enzymatic hydrolysis with savinase, a subtilisin-type enzyme.
Christiansen-Brams
I
I
Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark.
Jansson
A M
AM
Meldal
M
M
Breddam
K
K
Bock
K
K
D000595:Amino Acid Sequence; D001665:Binding Sites; D050260:Carbohydrate Metabolism; D002240:Carbohydrate Sequence; D003196:Computer Graphics; D005453:Fluorescence; D017611:Fluorine Compounds / Q000138:chemical synthesis; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012697:Serine Endopeptidases / Q000378:metabolism; D013381:Subtilisins / Q000378:metabolism*; D013402:Sugar Alcohols / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D017611:Fluorine Compounds; D006020:Glycopeptides; D013402:Sugar Alcohols; D014297:Trimethylsilyl Compounds; D012697:Serine Endopeptidases; D013381:Subtilisins; C032923:microbial serine proteinases; C014635:lactitol