252009-68-0Relevant articles and documents
Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
Mishra, Vivek K.,Buter, Jeffrey,Blevins, Molly S.,Witte, Martin D.,Van Rhijn, Ildiko,Moody, D. Branch,Brodbelt, Jennifer S.,Minnaard, Adriaan J.
supporting information, p. 5126 - 5131 (2019/07/03)
Diphosphatidyltrehalose (diPT) is an immunogenic glycolipid, recently isolated from Salmonella Typhi. Despite rigorous structure elucidation, the sn-position of the acyl chains on the glycerol backbone had not been unequivocally established. A stereoselective synthesis of diPT and its regioisomer is reported herein. Using a hybrid MS3 approach combining collisional dissociation and ultraviolet photodissociation mass spectrometry for analysis of the regioisomers and natural diPT, the regiochemistry of the acyl chains of this abundant immunostimulatory glycolipid was established.
Isolation, Synthesis, and Biological Activity of Chlorinated Alkylresorcinols from Dictyostelium Cellular Slime Molds
Kikuchi, Haruhisa,Ito, Ikuko,Takahashi, Katsunori,Ishigaki, Hirotaka,Iizumi, Kyoichi,Kubohara, Yuzuru,Oshima, Yoshiteru
, p. 2716 - 2722 (2017/11/06)
Eight chlorinated alkylresorcinols, monochasiol A-H (1-8), were isolated from the fruiting bodies of Dictyostelium monochasioides. Compounds 1-8 were synthesized to confirm their structures and to obtain sufficient material for performing biological tests. Monochasiol A (1) selectively inhibited the concanavalin A-induced interleukin-2 production in Jurkat cells, a human T lymphocyte cell line. Monochasiols were biogenetically synthesized by the combination of biosynthetic enzymes relating to the principal polyketides, MPBD and DIF-1, produced by Dictyostelium discoideum.
The synthesis of (11R,12S)-lactobacillic acid and its enantiomer
Coxon, Geoffrey D.,Al-Dulayymi, Juma R.,Baird, Mark S.,Knobl, Stefan,Roberts, Evan,Minnikin, David E.
, p. 1211 - 1222 (2007/10/03)
(11R,12S)-Lactobacillic acid has been prepared from 2,3-O-isopropylidene-D-glyceraldehyde, in a sequence involving asymmetric cyclopropanation, and from cis-cyclopropane-1,2-dimethanol, using enzymatic desymmetrisation. The key step in the former route wa
The synthesis of both enantiomers of lactobacillic acid and mycolic acid analogues
Coxon, Geoffrey D.,Knobl, Stefan,Roberts, Evan,Baird, Mark S.,Al Dulayymi, Juma R.,Besra, Gurdyal S.,Brennan, Patrick J.,Minnikin, David E.
, p. 6689 - 6692 (2007/10/03)
(11R, 12S)-Lactobacillic acid (1) has been prepared either from D- mannitol by asymmetric cyclopropanation or from cis-cyclopropane-1, 2- dimethanol by enzymatic desymmetrisation. The syntheses of (l1S 12R)- lactobacillic acid (2) and (1R, 2S) 1- (3'-methoxycarbonylpropyl)-2- octadecylcyclopropane (26) and related analogues (27 and 28) have also been achieved.