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2‐( N ‐Fmoc)‐3‐( N ‐Boc‐ N ‐methoxy)‐diaminopropanoic acid, an amino acid for the synthesis of mimics of O ‐linked glycopeptides
Author(s) -
Carrasco Michael R.,
Brown Ryan T.,
Doan Vu H.,
Kandel Sean M.,
Lee Franklin C.
Publication year - 2006
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20496
Subject(s) - chemistry , glycopeptide , amino acid , combinatorial chemistry , stereochemistry , biochemistry , antibiotics
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. © 2006 Wiley Periodicals, Inc. Biopolymers(Pept Sci) 84: 414–420, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com