2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid, an amino acid for the synthesis of mimics of O-linked glycopeptides.
Amino acids with N-alkylaminooxy side chains have proven effective for the rapid synthesis of neoglycopeptides. Chemoselective reaction of reducing sugars with peptides containing these amino acids provides glycoconjugates that are structurally similar to their natural counterparts. 2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl; Boc: t-butyloxycarbonyl) was synthesized from Boc-Ser-OH in >40% overall yield and incorporated into peptides by standard Fmoc chemistry based solid phase peptide synthesis. The resulting peptides are efficiently glycosylated and serve as mimics of O-linked glycopeptides. The synthesis of this derivative greatly expands the availability of the N-alkylaminooxy strategy for neoglycopeptides.
Carrasco
Michael R
MR
Department of Chemistry, Santa Clara University, Santa Clara, CA 95053-0270, USA. mcarrasco@scu.edu
Brown
Ryan T
RT
Doan
Vu H
VH
Kandel
Sean M
SM
Lee
Franklin C
FC
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*
D000596:Amino Acids; D005449:Fluorenes; D006020:Glycopeptides; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides