Unravelling the immunology of complex glycolipids by chemical synthesis

Synthesis and structure of clozapine N-oxide hemi(hydrochloride): an infinite hydrogen-bonded poly[n]catenane

Phillip L van der Peet, Rohan D Joyce, Holger Ott, Sebastian M Marcuccio, Jonathan M White, Spencer J Williams

2022-10-01

The structure of the title compound, 2C18H19ClN4O·HCl or (CNO)2·HCl (C36H39Cl3N8O2), at 100 K has tetra-gonal (I4/m) symmetry. The..

Chemogenetic inhibition of Phox2-expressing neurons in the commissural NTS decreases blood pressure in anesthetized spontaneously hypertensive rats.

Mariana Rosso Melo, Joshua J Voger, Angela A Connelly, Jaspreet K Bassi, Eduardo Colombari, Andrew M Allen

2022-09-14

Interruption of the activity of neurons in the commissural portion of the nucleus of the solitary tract (cNTS) decreases blood pre..

Helicobacter pylori metabolites exacerbate gastritis through C-type lectin receptors

Masahiro Nagata, Kenji Toyonaga, Eri Ishikawa, Shojiro Haji, Nobuyuki Okahashi, Masatomo Takahashi, Yoshihiro Izumi, Akihiro Imamura, Koichi Takato, Hideharu Ishida, Shigenori Nagai, Petr Illarionov, Bridget L Stocker, Mattie SM Timmer, Dylan GM Smith, Spencer J Williams, Takeshi Bamba, Tomofumi Miyamoto, Makoto Arita, Ben J Appelmelk

2021-01-04

Helicobacter pylori causes gastritis, which has been attributed to the development of H. pylori-specific T cells during infection...

Candida albicans steryl 6-O-acyl-alpha-d-mannosides agonize signalling through Mincle

Tram Nguyen, Yuki Hosono, Takashi Shimizu, Sho Yamasaki, Spencer J Williams

2020-12-11

The C-type lectin receptor Mincle binds Candida albicans and has been implicated in its pathobiology, but the molecular effectors ..

Cholesteryl 6-O-acyl-alpha-glucosides from diverseHelicobacterspp. signal through the C-type lectin receptor Mincle

Dylan GM Smith, Emi Ito, Sho Yamasaki, Spencer J Williams

2020-10-21

Helicobacter spp. are Gram-negative bacteria that cause a spectrum of disease in the gut, biliary tree and liver. Many Helicobacte..

Design of potent Mincle signalling agonists based on an alkyl beta-glucoside template

Dylan GM Smith, Yuki Hosono, Masahiro Nagata, Sho Yamasaki, Spencer J Williams

2020-04-21

The innate immune receptor Mincle senses lipid-based molecules derived from pathogens, commensals and altered self. Based on emerg..

alpha-Glucuronosyl and alpha-glucosyl diacylglycerides, natural killer T cell-activating lipids from bacteria and fungi

Satvika Burugupalli, Catarina F Almeida, Dylan GM Smith, Sayali Shah, Onisha Patel, Jamie Rossjohn, Adam P Uldrich, Dale I Godfrey, Spencer J Williams

2020-02-28

Natural killer T cells express T cell receptors (TCRs) that recognize glycolipid antigens in association with the antigen-presenti..

Distinct CD1d docking strategies exhibited by diverse Type II NKT cell receptors

Catarina F Almeida, Srinivasan Sundararaj, Jerome Le Nours, T Praveena, Benjamin Cao, Satvika Burugupalli, Dylan GM Smith, Onisha Patel, Manfred Brigl, Daniel G Pellicci, Spencer J Williams, Adam P Uldrich, Dale I Godfrey, Jamie Rossjohn

2019-11-20

Type I and type II natural killer T (NKT) cells are restricted to the lipid antigen-presenting molecule CD1d. While we have an und..

Distortion of mannoimidazole supports a B-2,B-5 boat transition state for the family GH125 alpha-1,6-mannosidase from Clostridium perfringens

Alexandra Males, Gaetano Speciale, Spencer J Williams, Gideon J Davies

2019-09-14

Enzyme transition-state mimics can act as powerful inhibitors and allow structural studies that report on the conformation of the ..

A Family of Dual-Activity Glycosyltransferase-Phosphorylases Mediates Mannogen Turnover and Virulence in Leishmania Parasites

M Fleur Sernee, Julie E Ralton, Tracy L Nero, Lukasz F Sobala, Joachim Kloehn, Marcel A Vieira-Lara, Simon A Cobbold, Lauren Stanton, Douglas EV Pires, Eric Hanssen, Alexandra Males, Tom Ward, Laurence M Bastidas, Phillip L van der Peet, Michael W Parker, David B Ascher, Spencer J Williams, Gideon J Davies, Malcolm J McConville

2019-09-11

Parasitic protists belonging to the genus Leishmania synthesize the non-canonical carbohydrate reserve, mannogen, which is compose..

Synthetic beta-1,2-Mannosyloxymannitol Glycolipid from the Fungus Malassezia pachydermatis Signals through Human Mincle

Phillip L van der Peet, Christian Gunawan, Miyuki Watanabe, Sho Yamasaki, Spencer J Williams

2019-06-07

Mincle is a C-type lectin receptor of the innate immune system with the ability to sense pathogens and commensals through lipidic ..

Eucalyptus subgenus Eucalyptus (Myrtaceae) trees are abundant sources of medicinal pinocembrin and related methylated flavanones

Jason QD Goodger, Samiddhi L Senaratne, Phillip van der Peet, Rhys Browning, Spencer J Williams, Dean Nicolle, Ian E Woodrow

2019-05-01

Plant-derived flavanones such as pinocembrin and related methylated forms are of interest for their potential medicinal use. Comme..

Sensing Lipids with Mincle: Structure and Function

Spencer J Williams

2017-11-27

Mincle is a C-type lectin receptor that has emerged as an important player in innate immunity through its capacity to recognize a ..

A carbon tetrachloride-free synthesis of N-phenyltrifluoroacetimidoyl chloride

Dylan GM Smith, Spencer J Williams

2017-10-10

N-Phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) is a reagent widely used for the preparation of glycosyl N-phenyltrifluoroacetimi..

Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

Satvika Burugupalli, Mark B Richardson, Spencer J Williams

2017-09-21

We report the total synthesis of (R)-tuberculostearic acid-containing Mycobacterium tuberculosis phosphatidylglycerol (PG). The ap..

Gas-Phase Intercluster Thiyl-Radical Induced C-H Bond Homolysis Selectively Forms Sugar C2-Radical Cations of Methyl D-Glucopyranoside: Isotopic Labeling Studies and Cleavage Reactions

Sandra Osburn, Gaetano Speciale, Spencer J Williams, Richard AJ O'Hair

2017-07-01

A suite of isotopologues of methyl D-glucopyranosides is used in conjunction with multistage mass spectrometry experiments to dete..

Selective Manipulation of Discrete Mannosidase Activities in the Endoplasmic Reticulum by Using Reciprocally Selective Inhibitors

Taiki Kuribara, Makoto Hirano, Gaetano Speciale, Spencer J Williams, Yukishige Ito, Kiichiro Totani

2017-06-01

Within the endoplasmic reticulum, immature glycoproteins are sorted into secretion and degradation pathways through the sequential..

Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae alpha-glucosyl diglyceride

Mark B Richardson, Dylan GM Smith, Spencer J Williams

2017-01-18

The fidelity of acylation regioselectivity in the synthesis of mixed glycosyl diacylglycerols can be accurately measured by quanti..

Total Synthesis of Mycobacterium tuberculosis Dideoxymy-cobactin-838 and Stereoisomers: Diverse CD1a-Restricted T Cells Display a Common Hierarchy of Lipopeptide Recognition

Janice MH Cheng, Ligong Liu, Daniel G Pellicci, Scott JJ Reddiex, Rachel N Cotton, Tan-Yun Cheng, David C Young, Ildiko Van Rhijn, D Branch Moody, Jamie Rossjohn, David P Fairlie, Dale I Godfrey, Spencer J Williams

2017-01-01

Mycobacterium tuberculosis produces dideoxymycobactin-838 (DDM-838), a lipopeptide that potently activates T cells upon binding to..

Lipid structure influences the ability of glucose monocorynomycolate to signal through Mincle

Phillip L van der Peet, Masahiro Nagata, Sayali Shah, Jonathan M White, Sho Yamasaki, Spencer J Williams

2016-01-01

Mincle (macrophage-inducible C-type lectin) is a C-type lectin receptor that provides the capacity for immune sensing of a range o..

Total synthesis of a cyclopropane-fatty acid alpha-glucosyl diglyceride from Lactobacillus plantarum and identification of its ability to signal through Mincle

Sayali Shah, Masahiro Nagata, Sho Yamasaki, Spencer J Williams

2016-01-01

We report a concise synthesis of glycolipid GL1 from Lactobacillus plantarum commencing from methyl α-d-glucopyroside. A Jacobsen ..