Document Detail

Synthesis and application of carbohydrate-derived morpholine amino acids.
MedLine Citation:
PMID:  15549804     Owner:  NLM     Status:  MEDLINE    
The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an epsilon-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.
Gijsbert M Grotenbreg; Alphert E Christina; Annelies E M Buizert; Gijsbert A van der Marel; Herman S Overkleeft; Mark Overhand
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Nov 
Date Detail:
Created Date:  2004-11-19     Completed Date:  2005-01-13     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:  8331-9     Citation Subset:  IM    
Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry
Carbohydrates / chemical synthesis,  chemistry*
Molecular Conformation
Morpholines / chemical synthesis,  chemistry*
Reg. No./Substance:
0/Amino Acids; 0/Carbohydrates; 0/Morpholines

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