Search results for "Serine methyl ester"

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Synthese von geschützten Serin-Glycopeptiden durch N-terminale Peptidketten-Verlängerung

1983

O-(2-Acetamido-3,4,6-tri-O-acetyl-2- desoxy-β-D-glucopyranosyl)serin-methylester (4) wird mit den 2-Phosphonioethoxycarbonyl-(Peoc-)Aminosauren 5 zu den voll geschutzten O-Glycodipeptiden 6 umgesetzt. Aus den Verbindungen 6 wird die Peoc-Gruppe mit Morpholin/Methylendichlorid vollstandig und selektiv zu 7 abgespalten, wobei weder β-Eliminierung des Kohlenhydratteils noch Esteraminolyse zu beobachten ist. Die N-deblockierten Glycodipeptide 7 reagieren mit den Peoc-Aminosauren 5 zu den geschutzten O-Glycotripeptiden 8. Mit Z-Asparagin (9) kann der Leucyl-(O-glycosyl)serinester 7a zum geschutzten Glycotripeptid 10 verknupft werden, das die fur N-Glycoproteine typische Sequenz -Asn-X-Ser- entha…

Serinechemistry.chemical_classificationchemistry.chemical_compoundAminolysischemistryStereochemistryMorpholineOrganic ChemistryPeptideGlycosylPhysical and Theoretical ChemistrySerine methyl esterAmino acidLiebigs Annalen der Chemie

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