3-Azi-1-methoxybutyl D-maltooligosaccharides Specifically Bind to the maltose/maltooligosaccharide-binding Protein of Escherichia Coli and Can Be Used as Photoaffinity Labels

Eur J Biochem. 1986 Oct 1;160(1):83-91. doi: 10.1111/j.1432-1033.1986.tb09943.x.


Maltooligosaccharides with two to six (alpha 1-4)-linked glucose residues, carrying at their reducing end a 3-azi-1-methoxybutyl group in either alpha or in beta glycosidic linkage, were synthesized. These maltooligosaccharide analogues inhibit maltose uptake via the maltose-binding-protein-dependent transport system in Escherichia coli. The concentration of half-maximal inhibition of maltose transport, at 15 nM concentration, decreases with increasing chain length of the analogue, levelling off at 40 microM after a chain length of four glucose residues in the alpha series and at 350 microM after a chain length of three glucose residues in the beta series. The inhibition of maltose transport occurs at the level of the periplasmic maltose-binding protein. 3-Azi-1-methoxybutyl alpha-D-[3H]maltotrioside was bound by the maltose-binding protein with a Kd of 0.18 mM. Irradiation at 350 nm of purified maltose-binding protein in the presence of 4 microM of this substrate labeled the protein covalently; labeling was prevented by 1 mM maltose. Using a crude preparation of periplasmic proteins two proteins were labeled, the maltose-binding protein and alpha-amylase. Thus, 3-azi-1-methoxybutyl alpha-D-maltooligosaccharides are potent photoaffinity labels for proteins with maltooligosaccharides-binding sites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP-Binding Cassette Transporters*
  • Affinity Labels / chemical synthesis*
  • Azides / chemical synthesis*
  • Azides / metabolism
  • Bacterial Proteins / metabolism*
  • Biological Transport / drug effects
  • Carrier Proteins / metabolism*
  • Escherichia coli / metabolism*
  • Escherichia coli Proteins*
  • Maltose / metabolism
  • Maltose-Binding Proteins
  • Monosaccharide Transport Proteins*
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / metabolism
  • Periplasmic Binding Proteins*
  • Photochemistry
  • Protein Binding


  • ATP-Binding Cassette Transporters
  • Affinity Labels
  • Azides
  • Bacterial Proteins
  • Carrier Proteins
  • Escherichia coli Proteins
  • MalE protein, E coli
  • Maltose-Binding Proteins
  • Monosaccharide Transport Proteins
  • Oligosaccharides
  • Periplasmic Binding Proteins
  • maltose transport system, E coli
  • Maltose