Malto-oligosaccharide homologues of 3,7-anhydro-2-azi-1,2-dideoxy-D-glycero-D-gulo-octitol+ ++: improved photoaffinity reagents for labelling the malto-oligosaccharide-binding protein of Escherichia coli.
3,7-Anhydro-2-azi-1,2-dideoxy-D-glycero-D-gulo-octitol (2) was synthesized as a beta-D-glucopyranosyl analogue, which could be converted into a series of malto-oligosaccharide derivatives (3-7) by cyclodextrinase-catalyzed glucosyl transfer from alpha-cyclodextrin (cyclomaltohexaose). The pure analogues 3-7 containing 1-5 (1----4)-linked alpha-D-glucose residues inhibited the uptake of maltose via the maltose-binding protein-dependent transport system in Escherichia coli. The concentration of half-maximal inhibition of maltose transport at 60nM decreases with increasing chain-length of the analogue, reaching a minimum at 0.02 mM for 6 (4 glucose residues). 3H-Labelled alpha-cyclodextrin was prepared by partial oxidation and reduction of the aldehyde groups with NaB3H4. Radiolabelled 5a was used to photolabel the binding site of the maltose-binding protein.
Lehmann
J
J
Institut für Organische Chemie und Biochemie der Universität, Freiburg i. Br., F.R.G.
Steck
J
J
Weiser
W
W
Boos
W
W
Wrissenberg
S
S
D018528:ATP-Binding Cassette Transporters; D000345:Affinity Labels / Q000138:chemical synthesis*; D001391:Azo Compounds / Q000138:chemical synthesis / Q000378:metabolism; D002352:Carrier Proteins / Q000378:metabolism*; D004926:Escherichia coli / Q000378:metabolism*; D029968:Escherichia coli Proteins; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000378:metabolism*; D058619:Maltose-Binding Proteins; D008565:Membrane Proteins / Q000378:metabolism*; D009004:Monosaccharide Transport Proteins; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000378:metabolism*; D009904:Optical Rotation; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000378:metabolism
D018528:ATP-Binding Cassette Transporters; D000345:Affinity Labels; D001391:Azo Compounds; D002352:Carrier Proteins; D029968:Escherichia coli Proteins; D058619:Maltose-Binding Proteins; D008565:Membrane Proteins; D009004:Monosaccharide Transport Proteins; D009844:Oligosaccharides; D013402:Sugar Alcohols; C021705:maltooligosaccharides; C461599:maltose transport system, E coli; D008320:Maltose