Are PhAcOZ and Nsc suitable N alpha-protecting groups for protease-catalysed peptide synthesis?
Protecting groups are necessary chemical tools in peptide synthesis. In protease-catalysed peptide synthesis they exert influence both on enzyme-substrate binding and on solubility. In this study, we have investigated the usability of various PhAcOZ- and Nsc-protected amino acids for protease-catalysed peptide synthesis. PhAcOZ-protected peptides were obtained in high yields using papain and thermolysin. In contrast to this, Nsc, as a base-labile alpha-amino protecting group, is not suitable for biocatalytic synthesis under the conditions employed.
Braun
K
K
Institute of Biochemistry, University of Technology, Dresden, Germany. Karin.Braun@chemie.tu-dresden.de
Kuhl
P
P
D000596:Amino Acids / Q000737:chemistry; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D010450:Endopeptidases / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D010206:Papain / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet; D013820:Thermolysin / Q000737:chemistry
C459519:4-phenylacetoxybenzyl glycine; D000596:Amino Acids; D001593:Benzyl Compounds; D007202:Indicators and Reagents; D010455:Peptides; D010450:Endopeptidases; D010206:Papain; D013820:Thermolysin; D005998:Glycine