Maltose and Maltotriose Derivatives as Potential Inhibitors of the Maltose‐Binding Protein

Abstract

Inhibition of substrate binding to maltose-binding protein (MBP) was investigated with structurally modified maltose and maltotriose derivatives that were designed based on the X-ray analysis of maltose and maltotriose bound to MBP. In maltose, positions 1a, 2a, 2b, 4b and 6b were modified (compounds 1-3, 18a, b, 28a-c, 39 and 44) of which only the trivalent maltose derivatives 39 and 44 exhibited high affinity to MBP. Maltotriose modifications were carried out at posi-

Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist

“…R f = 0.43 (25% EtOAc in hexanes); 1 H NMR (400 MHz, CDCl 3 ) 3.61 (t, J = 6.2 Hz, 2H), 3.76 (s, 6H), 4.24 (t, J = 6.2 Hz, 2H), 6.08 (d, J = 2.1 Hz, 2H), 6.10–6.12 (m, 1H); 13 C NMR (101 MHz, APT pulse sequence, CDCl 3 ) δ d 55.4, 93.61, 93.62; u 29.1, 67.9, 160.0, 161.6; IR (thin film): 1590, 1474, 1456 cm –1 . These data are in agreement with those previously reported …”

β -Alkylated oligomaltosides as new alternative preservatives: antimicrobial activity, cytotoxicity and preliminary investigation of their mechanism of action

“…Administration of a 2 g kg À1 of body weight dose to NMRI mice did not reveal any observable adverse effects (Weber and Benning 1984). Considering parabens and benzalkonium results, the results of our Figure 6 Schematic representation of maltose metabolism/transport in Escherichia coli (Boos and Shuman 1998) highlighting methyl-b-maltoside (MeG2), methyl-bmaltotrioside (MeG3) and methyl-bmaltotetraoside (MeG4) interactions, as reported in literature (Ferenci et al 1986;Malik et al 2008) or found in the present study (regardless of the microbial origin of tested enzymes/transporters).…”

“…; Malik et al . ) or found in the present study (regardless of the microbial origin of tested enzymes/transporters).…”

“…Journal of Applied Microbiology 115, 977--986 © 2013 The Society for Applied Microbiology pNPG conversion by a-glucosidase. Previous studies also reported an inhibition of key maltose metabolism enzymes or transporters by MeG2 and methyl-b-maltotetraoside (MeG4) such as the maltose-binding proteins (MBP) (Ferenci et al 1986;Malik et al 2008), the maltoporin (LamE) (Ferenci et al 1986) (Fig. 6) or the amylomaltase (EC 2.4.1.25) (Wiesmeyer and Cohn 1960).…”

Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O175 using one-pot glycosylations and its conformational analysis

“…Ethyl (2,3-di-O-benzyl-4,6-O-benzylidene-a-D-glucopyranosyl)-(1/4)-2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside (4), 20 prepared from D-maltose, was treated with acetic anhydride 21 in the presence of perchloric acid supported over silica gel (HClO 4 /SiO 2 ) 22 to furnish ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-a-D-glucopyranosyl)-(1/4)-2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside (5) in 80% yield (Scheme 1).…”