Iterative, aqueous synthesis of β3-oligopeptides without coupling reagents

Journal of the American Chemical Society

Volumn 128, Issue 5, 2006, Pages 1452-1453

  Carrillo, Nancy ^a   Davalos, Eric A ^a   Russak, Justin A ^a   Bode, Jeffrey W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOPEPTIDE; REAGENT;

AQUEOUS SOLUTION; ARTICLE; CHIRALITY; COUPLING FACTOR; CYCLOADDITION; DECARBOXYLATION; PEPTIDE ANALYSIS; PROTEIN PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

ISOXAZOLES; KETO ACIDS; OLIGOPEPTIDES; WATER;

EID: 32244438956     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057706j     Document Type: Article

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20. Enantiomeric purities and absolute configurations were confirmed by conversion to known compounds and by chiral HPLC studies.
21. For this study, we utilized a D-mannose-derived chiral auxiliary that afforded the "unnatural" peptide enantiomers. We have also prepared the "natural" enantiomers by using a chiral auxiliary derived from D-gulose. Further studies on the syntheses of these and other isoxazolidine monomers will be reported separately.