L-Glycero-D-mannoheptose, CAS:4305-74-2

L-Glycero-D-manno-heptoseL-Glycero-D-manno-heptose is a polymyxin B antimicrobial agent that has been shown to have significant activity against Gram-positive bacteria, including Staphylococcus aureus and Streptococcus pneumoniae. This compound also has an inhibitory effect on the growth of Gram-negative species such as Salmonella enterica. L-Glycero-D-manno-heptose inhibits the synthesis of bacterial cell wall peptidoglycan by binding to the terminal residues of oligosaccharides, which are linked to D-alanine in the peptidoglycan chain. The terminal residues of oligosaccharides are transferred from the lipid carrier to L-glycero-D manno heptose, forming a stable acylated glycoside. This reaction mechanism is similar to that of polymyxin B, but with a difference in reactivity due to steric hindrance.CAS Number4305-74-2Product Nameglycero-manno-HeptoseIUPAC Name(2S,3S,4R,5R,6S)-2,3,4,5,6,7-hexahydroxyheptanalMolecular FormulaC?H??O?Molecular Weight210.18 g/molInChIInChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h1,3-7,9-14H,2H2/t3-,4+,5-,6-,7+/m1/s1InChI KeyYPZMPEPLWKRVLD-BIVRFLNRSA-NSMILESC(C(C(C(C(C(C=O)O)O)O)O)O)OSolubility0.48 MSynonymsD-glycero-D-manno-heptose, glycero-manno-heptose, glycero-manno-heptose, (D-glycero-D-manno)-isomer, glycero-manno-heptose, (D-glycero-L-manno)-isomer, L-glycero-D-manno-heptoseCanonical SMILESC(C(C(C(C(C(C=O)O)O)O)O)O)OIsomeric SMILESC([C@@H]([C@H]([C@H]([C@@H]([C@@H](C=O)O)O)O)O)O)O CAS No: 4305-74-2 MDL No: MFCD00269999 Chemical Formula: C7H14O7 Molecular Weight: 210.18References: 1. Boons GJ, van der Klein PAM, van der Marel GA, van Boom JH, Recl. Trav. Chim. 1988, 108, p5072. Teuber M, et al., Biochemistry 1968, 7, 9, p33033. Brade H, Galanos C, Infec. Immun. 1983, 42, p2504. Balla E, Zamyatina A, Andreas Hofingera A, Kosma P, Carbohyd. Res. 2007, 342, 17, p2537-2545