Synthesis of N-Fmoc-O- (N'-Boc-N'-methyl)-aminohomoserine, an amino acid for the facile preparation of neoglycopeptides.
The synthesis of N-Fmoc-O-(N'-Boc-N'-methyl)-aminohomoserine in 35% overall yield from l-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.
Carrasco
Michael R
MR
Department of Chemistry, Santa Clara University, Santa Clara, California 95053-0270, USA. mcarrasco@scu.edu
Brown
Ryan T
RT
Serafimova
Iana M
IM
Silva
Oscar
O
D006023:Glycoproteins / Q000138:chemical synthesis*; D006714:Homoserine / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*
D006023:Glycoproteins; C474459:N-Fmoc-O- (N'-Boc-N'-methyl)-aminohomoserine; D010455:Peptides; D006714:Homoserine