Publications

Publications listed by year

2020

Braganza CD, Motozono C, Sonoda K-H, Yamasaki S, Shibata K, Timmer MSM, Stocker BL. ‘Agonistic or antagonistic mucosal-associated invariant T (MAIT) cell activity is determined by the 6-alkylamino substituent on uracil MR1 ligands’, 2020, Chem. Commun., 2020, in press. https://doi.org/10.1039/D0CC00247J

2019

Foster AJ, Kodar K, Timmer MSM, Stocker BL. ‘Ortho-substituted lipidated bratemicin derivative shows promising Mincle-mediated adjuvant activity.’ 2019 Org. Biomol. Chem., 2020, 18, 1015-1222. [Selected for cover]

Khan A, Braganza CD, Kodar K, Timmer MSM, Stocker BL. ‘Stereochemistry, lipid length and branching influences Mincle agonist activity of monoacylglycerides.’Org. Biomol. Chem., 2020, 18, 355-572. [Selected for cover]

Cheng JMH, Chee SH, Dolen Y, Verdoes M, Timmer MSM, Stocker BL. α-Galactosylceramide probe for monitoring α-galactosylceramide uptake by cells. Carbohydr. Res. 2019, 486, 1, 107840.

Braganza CD, Shibata K, Fujiwara A, Motozono C, Sonoda K, Yamasaki S, Stocker BL, Timmer MSM. ‘The effect of MR1 ligand glyco-analogues on mucosal-associated invariant T (MAIT) cell activation,’ Org. Bio. Chem. 2019, 17, 8992–9000 [Selected for cover]

Santoso KT, Menorca A, Cheung C-Y, Cook GM, Stocker BL, Timmer, MSM. ‘The synthesis and evaluation of quinolinequinones as anti-tubercular agents’, Bioorg. Med. Chem. 2019, 27, 3532-3545.

Wahi K, Kodar K, McConnell MJ, Harper JL, Timmer MSM, Stocker BL. ‘MSU crystals enhance TDB-mediated inflammatory macrophage IL-1b secretion’ Immunity, 2019, 42, 1129-1136.

Santoso KT, Cheung C.-Y, Hards K, Cook GM, Stocker BL, Timmer, MSM. ‘The synthesis and investigation of phthalazinones as anti-tubercular agents’, Chem Asian J. 2019, 14, 1278-1285. [Special Edition].

Stocker BL, Kodar K, Wahi K,Foster AJ, Harper JL, Mori D,Yamasaki S, Timmer MSM. ‘The Effects of Trehalose Glycolipid Presentation on Cytokine Production by GM-CSF Macrophages.’Glycoconjugate J., 2019, 36, 69.

2018

Braganza CD, Santoso KT, Dangerfield EM, La Flamme AC, Timmer MSM, Stocker BL. ‘Evaluation of anti a-d-Glcp-(1/4)-a-d-Glcp (GAGA4) IgM antibodies as a biomarker for multiple sclerosis.’ RSC Advances, 2018, 8, 28086–28093.

Bird JH, Khan AA, Nishimura N, Yamasaki S, Timmer MSM, Stocker BL. ‘Synthesis of Branched Trehalose Glycolipids and Their Mincle Agonist Activity.’ J. Org. Chem. 2018, 83, 7593.

Foster AJ, Nagata M, Lu X, Lynch AT, Omahdi Z, Ishikawa E, Yamasaki S, Timmer MSM, Stocker BL.‘Lipidated brartemicin analogues are potent Th1-stimulating vaccine adjuvants.’ J. Med. Chem. 2018, 61, 1045.

Braganza CD, Teunissen T, Timmer MSM, Stocker BL. ‘Identification and biological activity of synthetic macrophage inducible C-type lectin ligands.’ Front. Immunol., 2018, 8, 1940.

Khan A, Kodar K, Timmer MSM, Stocker BL. ‘Lipid length and iso-branching of trehalose diesters influences Mincle agonist activity.’ Tetrahedron, 2018, 12, 1269. [Invited]

Hunt-Painter A, Stocker BL, MSM Timmer. ‘The synthesis of molecular chaperone 2,5-dideoxy-2,5-imino-d-altritol via a diastereoselective reductive amination and carbamate annulation.’ Tetrahedron, 2018, 12, 1307. [Invited]

2017

Munneke S, Kodar K, Painter GF, Stocker BL, Timmer MSM. ‘The modular synthesis of multivalent-functionalised glycodendrons for the detection of lectins including DC-SIGN.’ RSC Advances, 2017, 7, 45260.

Kodar K, Harper JL, McConnell MJ, Timmer MSM, Stocker BL. ‘The Mincle ligand trehalose dibehenate differentially modulates M1-like and M2-like macrophage phenotype and function via Syk signalling.’ Immun. Inflam. Dis. 2017, 5, 503.

Hunt-Painter A, Moggré G-J, Tyler PC, Stocker BL, Timmer MSM. ‘Diastereo-selective carbamate annulation for the synthesis of 2,5-dideoxy-2,5-imino-glycitols.’ Chemistry Select, 2017, 2, 8028.

Munneke S, Dangerfield EM, Stocker BL, Timmer MSM. ‘The versatility of N-alkyl-methoxyamine bi-functional linkers for the preparation of glycoconjugates,’ Glycoconjugate J. 2017, 34, 633.

Munneke S, Hill JC, Timmer MSM, Stocker BL. ‘Synthesis and Hydrolytic Stability of N- and O-Methyloxyamine Linkers for the Synthesis of Glycoconjugates.’ Eur. J. Org. Chem. 2017, 3722.

2016

Behler-Janbeck F, Takano T, Maus R, Stolper J, Jonigk D, Tort Tarrés M, Fuehner T, Prasse A, Welte T, MSM Timmer, Stocker BL, Nakanishi Y, Miyamoto T, Yamasaki S, Maus UA. ‘C-type lectin Mincle recognizes glucosyl-diacylglycerol of Streptococcus pneumoniae and plays a protective role in pneumococcal pneumonia,’ PLoS Pathog 2016, 12(12): e1006038.

Koh J, Zou H,Mukherjee D, Lin S, Lim, Khiapeng J, Tan D, Stocker BL, Timmer MSM, Corkran HM, Lakshminarayanan R, Tan DTH, Cao D, Beuerman RW,Dick T, Liu S. ‘Amphiphilic Xanthones as a potent chemical entity of anti-mycobacterial agents with membrane-targeting properties.’ Eur. J. Med. Chem. 2016, 123, 684.

Heikal A, Hards K, Cheung J, Shean Tee Z, Timmer MSM, Stocker BL, Cook GM. ‘Activation of type II NADH by quinolinequinones mediates anti-tubercular cell death.’ J. Antimicrobial. Chemo. 2016,71, 2840.

Liu B, Novikova N, Simpson MC, Timmer MSM, Stocker BL, Söhnel T, Ware DC, Brothers PJ. ‘Lighting up sugars: fluorescent BODIPY-gluco-furanose and -septanose conjugates linked by direct B-O-C bonds.’ Org.Bio.Chem. 2016, 14, 5205.

Waghorne CL, Corkran HM, Niktab E, Baty JW, Berridge MV, Munkacsi AB, McConnell MJ, Timmer MSM, BL Stocker.N,N-Bis(glycityl)amines as anti-cancer drugs.’ Bioorg. Med. Chem. 2016, 24, 3932.[Invited submission]

Corkran HM, Dangerfield EM, Haslett GW, Stocker BL, Timmer MSM. ‘Synthesis and anti-tuberculosis activity of glycitylamines.’ Bioorg. Med. Chem.2016, 24, 693.

Munneke S, Stocker BL, Timmer MSM, Gainsford GJ. N-(2-Acetamido-2-deoxy-[beta]-D-glucopyranosyl)-N-(3-azidopropyl)-O-methylhydroxylamine. Acta Crystallo-graphica, 2016, 72 (Pt 3): 340.

2015 - 2014 (selected publications)

Timmer MSM, Sauvageau J, Foster AJ, Ryan J, Lagutin K, Shaw O, Harper JL, Sims IM, Stocker BL. “Discovery of lipids from B. longum subsp. infantis using whole cell MALDI analysis.”J. Org. Chem. 2014, 79, 7332-7341. DOI: 10.1021/jo501016c

Cheng JMH, Dangerfield EM, Timmer MSM, Stocker BL. “A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate.”, Org. Bioorg. Chem. 2014, 12, 2729-2736. DOI: 10.1039/c4ob00241e

Stocker BL, Timmer MSM. “Trehalose diesters, lipoteichoic acids and α-GalCer: using chemistry to understand immunology.” Carbohydr Res. 2014, 389, 3-11.DOI: 10.1016/j.carres.2013.08.030

Stocker BL, Khan AA, Chee SH, Kamena F, Timmer MSM. “On one leg: trehalose monoesters activate macrophages in a mincle-dependant manner.” ChemBioChem 2014, 15, 382-388.DOI: 10.1002/cbic.201300674

Corkran HM, Munneke S, Dangerfield EM, Stocker BL, Timmer MSM. “Applications and limitations of the I2-mediated carbamate annulation for the synthesis of piperidines: five- versus six-membered ring formation.” J. Org. Chem. 2013, 78, 9791-9802.DOI: 10.1021/jo401512h

Stocker BL, Timmer MSM. “Chemical Tools to Study the Biological Function of Glycolipids.” ChemBioChem 2013, 14, 1164-1184. DOI:10.1002/cbic.201300064

Stocker BL, Jongkees SAK, Win-Mason AL, Dangerfield EM, Withers SG, Timmer MSM.The ‘mirror-image’ postulate as a guide to the selection and evaluation of pyrrolidines as a-l-fucosidase inhibitors.”Carbohydrate Res. 2013, 367, 29-32. DOI: 10.1016/j.carres.2012.11.011

Khan AA, Kamena F, Timmer MSM, Stocker BL. ‘Development of a benzophenone and alkyne functionalised trehalose probe to study trehalose dimycolate binding proteins.’ Org. Bioorg. Chem. 2013, 11, 881-885. DOI: 10.1039/c2ob27257a

Sauvageau J, Ryan J, Lagutin K, Sims IM, Stocker BL, Timmer MSM. “Isolation and Structural Characterisation of the Major Glycolipids from Lactobacillus plantarum.” Carbohydr. Res. 2012, 357, 151-156.DOI: 10.1016/j.carres.2012.05.011

Sauvageau J, Foster AJ, Khan AA, Chee SH, Sims IM, Timmer MSM, Stocker BL. “Synthesis and Biological Activity of the LTA glycolipid anchor from Streptococcus sp. DSM 8747.” ChemBioChem, 2012, 13, 2416-2424.DOI: 10.1002/cbic.201200468

Khan AA, Chee SH, Stocker BL, Timmer MSM. “The Synthesis of Long-Chain α-Alkyl-β-Hydroxy Esters Using Allylic Halides in a Fráter-Seebach Alkylation.” Eur. J. Org. Chem. 2012, 995-1002.DOI: 10.1002/ejoc.201101472

Stocker BL, Win-Mason AL, Timmer MSM. “I2-mediated carbamate annulation: scope and application in the synthesis of azasugars”, Carbohydr. Res., 2012, 356, 163–171.DOI: 10.1016/j.carres.2012.03.015

Dangerfield EM, Cheng JMH, Knight DA, Weinkove R, Dunbar PR, Hermans IF, Timmer MSM, Stocker BL. “Specific Activity of Glycolipid Ligands for Invariant NKT Cells.” ChemBioChem 2012, 13, 1349-1356.DOI:10.1002/cbic.201200095

Khan AA, Stocker BL, Timmer MSM. “Trehalose Glycolipids - Synthesis and Biological Activities.” Carbohydr. Res. 2012, 356, 25-36.DOI: 10.1016/j.carres.2012.03.010

Khan AA, Chee SH, McLaughlin RJ, Harper JL, Kamena F, Timmer MSM, Stocker BL. “Long-Chain Lipids Are Required for the Innate Immune Recognition of Trehalose Diesters by Macrophages.” ChemBioChem 2011, 3, 2572-2576.DOI: 10.1002/cbic.201100451 [Featured on the cover]

Timmer MSM, Dangerfield EM, Cheng JMH, Gulab SA, Stocker BL. “Rapid Synthesis of 1-Deoxygalactonojirimycin using a Carbamate Annulation.” Tetrahedron Lett. 2011, 52, 4803-4805.DOI: 10.1016/j.tetlet.2011.07.044

Win-Mason AL, Jongkees SAK, Withers SG, Tyler PC, Timmer MSM, Stocker BL. “Stereoselective total synthesis of aminoiminohexitols via carbamate annulation.” J. Org. Chem. 2011, 76, 9611-9621.DOI: 10.1021/jo201151b

Win-Mason AL, Dangerfield EM, Tyler PC, Stocker BL, Timmer MSM. “Stereoselective Strecker and Carbamate Annulation Methodology for the Synthesis of 1-Amino-1,2,5-trideoxy-2,5-imino-L-iditol.” Eur. J. Org. Chem. 2011, 4008-4014.DOI: 10.1002/ejoc.201100523

Cheng JMH, Chee SH, Knight DA, Acha-Orbea H, Hermans I, Timmer MSM, Stocker BL. “An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells.” Carbohydr. Res. 2011 , 346 , 914–926.DOI: 10.1016/j.carres.2011.02.014

Cheng JMH, Gulab SA, Timmer MSM, Stocker BL, Gainsford GJ. “Methyl 6-azido-6-deoxy-α-d-galactoside.”Acta Cryst. 2011, E67, o1941-o1942.DOI:10.1107/S1600536811025323

Cheng JMH, Kahn AA, Timmer MSM, Stocker BL. “Endogenous and exogenous CD1-binding glycolipids.” Int. J. Carbohydr. Chem. 2011, Article ID 749591, 13 p.DOI: 10.1155/2011/749591

Dangerfield EM, Plunkett CH, Win-Mason AL, Stocker BL, Timmer MSM. “Protecting-Group-Free Synthesis of Amines: Synthesis of Primary Amines from Aldehydes via Reductive Amination.” J. Org. Chem. 2010 , 75 , 5470-5477. DOI:10.1021/jo100004c

Dangerfield EM, Gulab SA, Plunkett CH, Timmer MSM, Stocker BL . “A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines.” Carbohydr. Res. 2010, 345, 1360-1365. DOI: 10.1016/j.carres.2010.03.016

Stocker BL, Dangerfield EM, Win-Mason AL, Haslett GW,Timmer MSM. “Recent developments in the synthesis of pyrrolidine-containing iminosugars,” Eur. J. Org. Chem. 2010, 1615-1637. DOI: 10.1002/ejoc.200901320 [Featured on the cover]

Dangerfield EM, Win-Mason AL, Timmer MSM, Stocker BL. “Tuberculosis: Bugs vs Drugs Part 1.” Chem. Aus., 2010, 77(4), 22-26. Document

Gulab SA, Cheng JMH, Timmer MSM, Stocker BL, Gainsford GJ.“Methyl 6-deoxy-6-iodo-α-d-galactoside.” Acta Crystallogr., Sect. E: Struct. Rep. Online 2010  , 66, O1724-U738. DOI:

Khan AA, Cheng JMH, Stocker BL, Timmer MSM. “Glycolipids and CD1: The Crossroad between Chemistry and Immunology” Chem. New Zealand 2010, 74(2), 57-62.Document

Mulchin BJ, Newton CG, Baty JW, Grasso CH, Martin WJ, Walton MC, Dangerfield EM, Plunkett CH, Berridge MV, Harper JL, Timmer MSM, Stocker BL. “The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones.” Bioorg. Med. Chem. 2010 , 18 , 3238-3251. DOI: 10.1016/j.bmc.2010.03.021

Dangerfield EM, Win-Mason AL, Timmer MSM, Stocker BL.“Tuberculosis: Bugs vs Drugs Part 2.” Chem. Aus., 2010, 77(5), 17-21. Document

Dangerfield EM, Plunkett CH, Stocker BL, Timmer MSM. “Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars.” Molecules 2009, 14, 5298-5307. DOI:10.3390/molecules14125298

Timmer MSM, Stocker BL, Northcote PT, Burkett BA. “Azulene: A colourful protecting group.” Tetrahedron Lett. 2009, 50, 7199-7204.DOI: 10.1016/j.tetlet.2009.10.043

Baird LJ, Timmer MSM, Teesdale-Spittle PH, Harvey JE. “Total Synthesis of Aigialomycin D using a Ramberg-Bäcklund/RCM Strategy.” J. Org. Chem. 2009, 74, 2271-2277.DOI: 10.1021/jo802561s

Dangerfield EM, Timmer MSM, Stocker BL. “Total synthesis without protecting groups: pyrrolidines and cyclic carbamates.”Org. Lett. 2009, 11, 535-538.DOI: 10.1021/ol802484y

Dangerfield EM, Win-Mason AL, Timmer MSM, Stocker BL. “Tuberculosis drugs: Past, Present and Future.” ChemED NZ. 2009, 116, 3-7.

Adibekian A, Timmer MSM, Stallforth P, Van Rijn J, Wertz DB, Seeberger PH. “Stereocontrolled synthesis of fully functionalized D-glucosamine monosaccharides via a domino nitro-Michael/Henry reaction.” Chem. Commun. 2008, 30, 3549-3551.DOI: 10.1039/b805159c

Blackie E, Le Ru EC, Meyer M, Timmer M, Burkett B, Northcote P, Etchegoin, PG.“Bi-Analyte SERS with isotopically edited dyes.” Phys. Chem. Chem. Phys. 2008, 10, 4147-4153.DOI: 10.1039/b803738h [Featured on the cover]

Adibekian A, Bindschädler P, Timmer MSM, Noti C, Schützenmeister N and Seeberger PH. “De Novo Synthesis of Uronic Acid Building Blocks for Assembly of Heparin Oligosaccharides.”Chem. Eur. J. 2007, 13, 4510-4522.DOI: 10.1002/chem.200700141

Timmer MSM, Stocker BL, Seeberger, PH. “Probing glycomics.” Curr. Opin. Chem. Biol. 2007, 11, 59-65.DOI: 10.1016/j.cbpa.2006.11.040

Lastdrager B, Timmer MSM, Van der Marel GA, Overkleeft HS, Overhand M. “Transformation of glucose into a novel carbasugar amino acid dipeptide isoster.” J. Carbohydr. Chem. 2007, 26, 41-59. DOI: 10.1080/07328300701252623

Timmer MSM, Stocker BL, Seeberger PH. “De novo synthesis of aceric acid, an aceric acid building block.” J. Org. Chem. 2006, 71, 8294-8297.DOI: 10.1021/jo061607m

Timmer MSM, Viciano Chumillas M, Donker-Koopman WE, Aerts JMFG, Van der Marel GA, Overkleeft HS, Van Boom JH. “Selective cross-metathesis of C-allyl-glycosides. J. Carbohydr. Chem. 2005, 24, 335-351.DOI: 10.1080/07328300500174877

Timmer MSM, Adibekian A, Seeberger PH. “Short de novo synthesis of fully functionalized uronic acid monosaccharides.” Angew. Chem. Int. Ed. 2005, 44, 7605-7607.DOI: 10.1002/anie.20052742

Timmer MSM, Risseeuw MDP, Verdoes M, Filippov DV, Plaisier JR, Van der Marel GA, Overkleeft HS, Van Boom JH. “Synthesis of functionalized heterocycles via a tandem Staudinger/aza-Wittig/Ugi multicomponent reaction.” Tetrahedron-Asymmetry 2005, 16, 177-185.DOI: 10.1016/j.tetasy.2004.11.079

Lastdrager B, Timmer MSM, Van der Marel GA, Overkleeft HS. “Claisen self-condensation/decarboxylation as the key steps in the synthesis of C2-symmetrical 1,7-dioxaspiro[5.5]undecanes.”Tetrahedron Lett. 2005, 46, 6195-6198.DOI: 10.1016/j.tetlet.2005.07.073

Timmer MSM, Verhelst SHL, Grotenbreg GM, Overhand M, Overkleeft HS. “Carbohydrates as versatile platforms in the construction of small compound libraries.”Pure Appl. Chem. 2005, 77, 1173-1181.DOI: 10.1351/pac200577071173

Litjens REJN, Den Heeten R, Timmer MSM, Overkleeft HS, Van der Marel GA. “An expedient synthesis of the repeating unit of the acidic polysaccharide of the bacteriolytic complex of lysoamidase.”Chem.-Eur. J. 2005, 11, 1010-1016.DOI: 10.1002/chem.200400862

Timmer MSM, Codee JDC, Overkleeft HS, Van Boom JH, Van der Marel GA. “A tandem ring-closing metathesis cleavable linker system for solid-phase oligosaccharide synthesis.”Synlett 2004, 12, 2155-2158.DOI: 10.1055/s-2004-831301

Grotenbreg GM, Kronemeijer M, Timmer MSM, El Oualid F, Van Well RM, Verdoes M, Spalburg E, Van Hooft PAV, De Neeling AJ, Noort D, Van Boom JH, Van der Marel GA, Overkleeft HS, Overhand M. “A practical synthesis of gramicidin S, sugar amino acid containing analogues.” J. Org. Chem. 2004, 69, 7851-7859. DOI: 10.1021/jo0487449

Grotenbreg GM, Timmer MSM, Llamas-Saiz AL, Verdoes M, Van der Marel GA, Van Raaij MJ, Overkleeft HS, Overhand M. “An unusual reverse turn structure adopted by a furanoid sugar amino acid incorporated in gramicidin S.” J. Am. Chem. Soc. 2004, 126, 3444-3446.DOI: 10.1021/ja0397254

Timmer MSM, Verdoes M, Sliedregt LAJM, Van der Marel GA, Van Boom JH, Overkleeft HS. “The use of a mannitol-derived fused oxacycle as a combinatorial scaffold.”J. Org. Chem. 2003, 68, 9406–9411.DOI: 10.1021/jo0349429

Verhelst SHL, Martinez BP, Timmer MSM, Lodder G, Van der Marel GA, Overkleeft HS, Van Boom JH. “A short route toward chiral, polyhydroxylated indolizidines, quinolizidines.”J. Org. Chem. 2003, 68, 9598-9603.DOI: 10.1021/jo0349429

Timmer MSM, Ovaa H, Filippov DV, Van der Marel GA and Van Boom JH. “Synthesis of phosphorus mono- and bicycles by catalytic ring-closing metathesis.”Tetrahedron Lett. 2001, 42, 8231-8233.DOI: 10.1016/S0040-4039(01)01740-3

Timmer MSM, Ovaa H, Filippov DV, Van der Marel GA and Van Boom JH. “An expeditious route to phosphorus heterocycles based on ring-closing metathesis.”Tetrahedron Lett. 2000, 41, 8635-8638.DOI: 10.1016/S0040-4039(00)01511-2

Patents

Stocker BL, Timmer MSM, Yamasaki S, Foster AJ. Brartemicin Analogues. PCT/NZ2018/050156. November 2, 2018.

Bird JH, Timmer MSM, Stocker BL. Branched Trehalose Glycolipids. PCT/NZ2018/050157. November 2, 2018.

‘Synthetic Methods and Compositions’. EM Dangerfield, MSM Timmer, BL Stocker. Reference: 586619 DDG. Provisional filed: October 2008, full 10th Oct 2009.