Publications Mattie Timmer
1.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
2. 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
3. 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
4. Stocker BL, Khan AA, Chee SH, Kamena F, Timmer MSM. “On one leg: trehalose monoesters activate macrophages in a mincle-dependent manner.” ChemBioChem 2014 , 15 , 382-388. DOI: 10.1002/cbic.201300674
5. 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
6. Stocker BL, Timmer MSM. “Chemical Tools to Study the Biological Function of Glycolipids.” ChemBioChem 2013, 14 , 1164-1184. DOI:10.1002/cbic.201300064
7. 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
8. 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
9. 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
10. 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
11. 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
12. 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
13. 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
14. 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
15. 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]
16. 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
17. 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
18. 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
19. 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
20. 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
21. 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
22. 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
23. 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
24. 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]
25. Dangerfield EM, Win-Mason AL, Timmer MSM, Stocker BL. “Tuberculosis: Bugs vs Drugs Part 1.” Chem. Aus. , 2010, 77(4), 22-26. Document
26. 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:
27. 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
28. 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
29. Dangerfield EM, Win-Mason AL, Timmer MSM, Stocker BL.“Tuberculosis: Bugs vs Drugs Part 2.” Chem. Aus. , 2010, 77(5) , 17-21. Document
30. Dangerfield EM, Plunkett CH, Stocker BL, Timmer MSM. “Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars.” Molecules2009 , 14 , 5298-5307. DOI:10.3390/molecules14125298
31. 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
32. 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
33. 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
34. Dangerfield EM, Win-Mason AL, Timmer MSM, Stocker BL. “Tuberculosis drugs: Past, Present and Future.” ChemED NZ. 2009 , 116, 3-7.
35. 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
36. 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]
37. 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
38. Timmer MSM, Stocker BL, Seeberger, PH. “Probing glycomics.” Curr. Opin. Chem. Biol. 2007 , 11, 59-65.DOI: 10.1016/j.cbpa.2006.11.040
39. 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
40. 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
41. 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
42. 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
43. 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
44. 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
45. 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
46. 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
47. 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
48. 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
49. 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
50. 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
51. 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
52. 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. 2 001 , 42 , 8231-8233. DOI: 10.1016/S0040-4039(01)01740-3
53. 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