Synthesis and application of carbohydrate-derived morpholine amino acids

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8331-8339

  Grotenbreg, Gijsbert M ^a   Christina, Alphert E ^a   Buizert, Annelies E M ^a   Van Der Marel, Gijsbert A ^a   Overkleeft, Herman S ^a   Overhand, Mark ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CARBOHYDRATES; GLYCOLS; OXIDATION; POLYPEPTIDES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CLEAVAGE; MORPHOLINE; OXIDATIVE GLYCOL; REDUCTIVE AMINATION;

AMINO ACIDS;

AMINO ACID; CARBOHYDRATE; GLYCOL; MORPHOLINE DERIVATIVE; OLIGOPEPTIDE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; REDUCTION; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CARBOHYDRATES; MOLECULAR CONFORMATION; MORPHOLINES; STEREOISOMERISM;

EID: 9344231985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048630x     Document Type: Article

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44. α) for the proteinogenic residues in peptide 20 follow a similar trend compared to native GS. These distinctive features validate a β-sheet conformation in GS analogues, as we have previously observed: Grotenbreg, G. M.; Kronemeijer, M.; Timmer, M. S. M.; El Oualid, F.; van Well, R. M.; Verdoes, M.; Spalburg, E.; van Hooft, P. A. V.; de Neeling, A. J.; Noort, D.; van Boom, J. H.; van der Marel, G. A.; Overkleeft H. S.; Overhand, M. J. Org. Chem., in press.
45. To facilitate the characterization of GS analogue 21, a small aliquot was deprotected and purified by reversed-phase HPLC to produce the unprotected peptide in 69% yield.