Synthesis and application of an auxiliary group for chemical ligation at the X-gly site.
An efficient synthesis of an auxiliary group, the 2-mercapto-4,5-dimethoxybenzyl (Dmmb) moiety, to form a Gly-building block is presented. The building block was incorporated into peptides to study the reaction with thiobenzyl-activated derivatives. The target peptides have been obtained by standard chemical ligation reaction, followed by TMSBr-assisted cleavage to remove the auxiliary group. Prior to Dmmb removal, under acidic conditions an unexpected rearrangement was observed and evidence for a mechanism is provided.
Vizzavona
Jean
J
BACHEM AG, Hauptstrasse 144, CH-4416 Bubendorf, Switzerland.
Dick
Fritz
F
Vorherr
Thomas
T
D000595:Amino Acid Sequence; D001596:Benzylamines / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D005998:Glycine / Q000737:chemistry*; D007700:Kinetics; D013058:Mass Spectrometry / Q000379:methods; D010455:Peptides / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D001596:Benzylamines; D010455:Peptides; D013438:Sulfhydryl Compounds; D014297:Trimethylsilyl Compounds; D005998:Glycine