Document Detail

Synthesis of N-Fmoc-O- (N'-Boc-N'-methyl)-aminohomoserine, an amino acid for the facile preparation of neoglycopeptides.
MedLine Citation:
PMID:  12515483     Owner:  NLM     Status:  MEDLINE    
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.
Michael R Carrasco; Ryan T Brown; Iana M Serafimova; Oscar Silva
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  68     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2003 Jan 
Date Detail:
Created Date:  2003-01-07     Completed Date:  2003-06-20     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  195-7     Citation Subset:  IM    
Department of Chemistry, Santa Clara University, Santa Clara, California 95053-0270, USA.
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MeSH Terms
Glycoproteins / chemical synthesis*
Homoserine / analogs & derivatives,  analysis,  chemical synthesis*
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides / chemical synthesis*
Reg. No./Substance:
0/Glycoproteins; 0/N-Fmoc-O- (N'-Boc-N'-methyl)-aminohomoserine; 0/Peptides; 498-19-1/Homoserine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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