74501-32-9Relevant academic research and scientific papers
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.
, p. 5126 - 5131 (2019)
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.
The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle
Jacobsen, Kristian M.,Keiding, Ulrik B.,Clement, Lise L.,Schaffert, Eva S.,Rambaruth, Neela D. S.,Johannsen, Mogens,Drickamer, Kurt,Poulsen, Thomas B.
supporting information, p. 647 - 652 (2015/04/27)
We demonstrate that the natural product brartemicin, a newly discovered inhibitor of cancer cell invasion, is a high-affinity ligand of the carbohydrate-recognition domain (CRD) of the C-type lectin mincle. Recent studies have revealed that mincle is a ke
Synthesis and structure - Activity relationships studies of brartemicin analogs as anti-invasive agents
Jiang, Yong-Li,Miyanaga, Satoshi,Han, Xiu-Zhen,Tang, Long-Qiang,Igarashi, Yasuhiro,Saiki, Ikuo,Liu, Zhao-Peng
, p. 531 - 537 (2013/10/21)
Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to find more potent anti-invasive agents and study the structure-activity relationships, a series of 19 brartemicin analogs we
Self-assembling properties of 6-O-alkyltrehaloses under aqueous conditions
Kanemaru, Manami,Yamamoto, Kazuya,Kadokawa, Jun-Ichi
experimental part, p. 32 - 40 (2012/09/21)
In this study, we report the self-assembling properties of 6-O-alkyltrehaloses with different chain lengths, that is, octyl, decyl, dodecyl, tetradecyl, and hexadecyl, under aqueous conditions. The materials were synthesized from trehalose via five reacti
Self-assembling property of 6,6'-Di-O-octyltrehalose under aqueous conditions
Kanemaru, Manami,Yamamoto, Kazuya,Kadokawa, Jun-Ichi
, p. 954 - 956,3 (2020/08/31)
In this study, we synthesized a new trehalose-based amphiphile, 6,6'-di-O-octyltrehalose, from trehalose by five reaction steps. The SEM and TEM images of the sample prepared by drying its aqueous dispersion showed the formation of morphologically control
Synthesis and evaluation of trehalose-based compounds as anti-invasive agents
Jiang, Yong-Li,Tang, Long-Qian,Miyanaga, Satoshi,Igarashi, Yasuhiro,Saiki, Ikuo,Liu, Zhao-Peng
scheme or table, p. 1089 - 1091 (2011/04/16)
Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to explore the preliminary structure-activity relationship and obtain more potent inhibitors, a series of brartemicin analogs
Synthesis of a trehalose homolog, 6-deoxy-α-D-gluco-heptopyranosyl 6-deoxy-α-D-gluco-heptopyranoside, and the corresponding bis(heptosiduronic acid)
Baer, Hans H.,Breton, Roger L.,Shen, Yaping
, p. 377 - 389 (2007/10/02)
Crystalline 6-deoxy-α-D-gluco-heptopyranosyl 6-deoxy-α-D-gluco-heptopyranoside (8) and (6-deoxy-α-D-gluco-heptopyranosyluronic acid) 6-deoxy-α-D-gluco-heptopyranosiduronic acid (7) were synthesized from α,α-trehalose (1).Reaction of 2,3,4,2',3',4'-hexa-O-
