Synthesis of [6"-3H]-, (6"-2H)- and (2-2H)-maltotriose.
To prepare labeled precursors for biosynthetic studies, methods for the specific introduction of tritium and deuterium into the reducing and the terminal glucose unit of maltotriose were developed. Thus [6"-3H]- and (6"-2H)-maltotriose (17) and (18) were prepared via selective methoxytritylation, deprotection and subsequent modified Pfitzner-Moffatt oxidation, followed by reduction with sodium borotritiide or sodium borodeuteride, respectively. A simple two step procedure utilizing the Lobry de Bruyn/van Ekenstein transformation gave (2-2H)maltotriose (20).
Sauerbrei
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Department of Chemistry, University of Washington, Seattle 98195-1700, USA.
Niggemann
J
J
Gröger
S
S
Lee
S
S
Floss
H G
HG
D002240:Carbohydrate Sequence; D003903:Deuterium; D007553:Isotope Labeling / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D014312:Trisaccharides / Q000138:chemical synthesis*; D014316:Tritium; D001614:beta-Amylase / Q000378:metabolism
D014312:Trisaccharides; D014316:Tritium; C008317:maltotriose; D003903:Deuterium; D001614:beta-Amylase