Synthesis of N-Fmoc-O- (N‘-Boc-N‘-methyl)-aminohomoserine, an Amino Acid for the Facile Preparation of Neoglycopeptides
- 21 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (1) , 195-197
- https://doi.org/10.1021/jo026641p
Abstract
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.Keywords
This publication has 9 references indexed in Scilit:
- Synthesis of neoglycopeptides by chemoselective reaction of carbohydrates with peptides containing a novel N′-methyl-aminooxy amino acidTetrahedron Letters, 2002
- Asparagine surrogates for the assembly of N-linked glycopeptide mimetics by chemoselective ligationTetrahedron Letters, 2001
- Preparation and application ofO-amino-serine, Ams, a new building block in chemoselective ligation chemistryJournal of Peptide Science, 1999
- Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugatesTetrahedron, 1998
- Chemoselectively addressable HCan building blocks in peptide synthesis:L-homocanaline derivativesJournal of Peptide Science, 1998
- Synthesis of Glycopeptides and Lipopeptides by Chemoselective LigationAngewandte Chemie International Edition in English, 1996
- Mild palladium (O)-catalyzed deprotection of allyl esters. A useful application in the synthesis of carbapenems and other β-lactam derivatives.Tetrahedron Letters, 1987
- Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of aminesTetrahedron Letters, 1985
- Transfer of Chirality in the Addition of Chiral α‐Chloroallylboronate Esters to AldehydesAngewandte Chemie International Edition in English, 1984