Associate Professor Dr. Tirayut Vilaivan

 

Contact Information:

Department of Chemistry, Faculty of Science
Chulalongkorn University
Phayathai Road, Patumwan
Bangkok 10330, THAILAND

 

Office: 1340 Mahamakut Building
Tel: 02-2187627 ext 101
Fax: 02-2187598
E-mail: vtirayut@chula.ac.th

 

 

Personal Home Page:  

 

Teaching/Research Field:

Organic Chemistry

Research Unit(s):

Organic Synthesis Research Unit

 

 

 

Current Research Topics:

·        Synthesis and nucleic acid binding properties of Peptide Nucleic Acids (PNA)

·        Development of novel synthetic methodologies (esp. catalytic asymmetric synthesis)

·        Development of novel antimalarials based on Dihydrofolate Reductase inhibitors

 

Education:

·        1992 B.Sc. (Chemistry), Chulalongkorn University, THAILAND

·        1996 D.Phil (Organic Chemistry), Oxford University, UK

 

Work Experiences:

·        1996-1999 Lecturer, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, THAILAND

·        1999-2004 Assistant Professor, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, THAILAND

·        2004-present Associate Professor, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, THAILAND

 

Professional Services:

·        Membership Thai Academy of Science and Technology Foundation (Associate member: 2004-2006, Elected Member Oct 2006-present), American Chemical Society (2006-present), Science Society of Thailand, Chemical Society of Thailand.

·        International Editorial Advisory Board: Chemistry – An Asian Journal  (2010-present)

 

Selected Scholarship and Awards:

·        Apr–Sep 1998 Royal Society Research Fellowship (Dyson Perrins Laboratory, Oxford under supervision of Prof. G. Lowe, FRS) and visiting research fellow at Lincoln College, Oxford

·        2000 National Young Scientist Award (Science and Technology Promotion Foundation under patronage of HM King Bhumipol)

·        2009 CST Award for Distinguished Young Chemist 2008 (Chemical Society of Thailand)

·        2009–2011 Alexander von Humboldt fellowship for experienced researcher (Prof. Dr. Oliver Reiser (Regensburg) and Prof. Dr. Hans-Achim Wagewnknecht (Karlsruhe)

·        2009 TRF Senior Research Scholar (the Thailand Research Fund)

·        2011 National Distinguished Researcher 2010 (Chemical and Pharmaceutical Sciences) (National Research Council of Thailand)

 

Publications:

1.       Lowe, G.; McCloskey, J.A.; Ni, J.; Vilaivan, T. "A mass spectrometric investigation of the reaction between 4,4'-vinylidenedipyridine bis[2,2':6',2"-terpyridineplatinum(II)] and the self-complementary oligonucleotide d(CpGpTpApCpG)" Bioorg. Med. Chem. 1996, 4, 1007–1013.

2.       Lowe, G.; Vilaivan, T. " Reaction of 4-picoline(2,2':6',2"-terpyridine)platinum(II) with nucleosides" J. Chem. Soc., Perkin Trans I 1996, 1499–1503.

3.       Lowe, G.; Vilaivan, T. " An improved method for the synthesis of (2,2':6',2"-terpyridine)platinum(II) complexes" J. Chem. Res.(S) 1996, 386–387.

4.       Charnega, A.; Droz, A.S.; Prout, K.; Vilaivan, T.; Weaver, G.W.; Lowe, G. "Structural evidence for the reactivity of 4-picoline(2,2':6',2"-terpyridine)platinum(II) complexes and evidence for pi-stacking in the crystal lattice" J. Chem. Res.(S) 1996, 402–403.

5.       Lowe, G.; Vilaivan, T. "Amino acids bearing nucleobases for synthesis of novel peptide nucleic acids" J. Chem. Soc., Perkin Trans. I 1997, 539–546.

6.       Lowe, G.; Vilaivan, T. "Dipeptides bearing nucleobases for synthesis of novel peptide nucleic acids" J. Chem. Soc., Perkin Trans. I 1997, 547–554.

7.       Lowe, G.; Vilaivan, T. "Solid phase synthesis of novel peptide nucleic acids" J. Chem. Soc., Perkin Trans. I 1997, 555–560.

8.       Lowe, G.; Vilaivan, T.; Westwell, M.S. "Hybridization studies with chiral peptide nucleic acids" Bioorg. Chem. 1997, 25(5-6), 321–329.

9.       Roengsumran, S.; Achayindee, S.; Petsom, A.; Pudhom, K.; Singtothong, P.; Surachetapan, C.; Vilaivan, T. "Two new cembranoids from Croton oblongifolius" J. Nat. Prod. 1998, 61(5), 652-654.

10.     Roengsumran, S.; Petsom, A.; Sommit, D.; Vilaivan, T. "New labdane diterpenoids from Croton oblongifolius" Phytochemistry 1999, 50, 449–453.

11.     Lowe, G.; Droz, A.S.; Vilaivan, T.; Weaver, G.W.; Tweedale, L.; Pratt, J.M.; Rock, P.; Yardley, V.; Croft, S.L. "Cytotoxicity of (2,2':6',2"-terpyridine)platinum(II) complexes to Leishmania donovani, Trypanosoma cruzi and Trypanosoma brucei" J. Med. Chem. 1999, 42(6), 999–1006.

12.     Pudhom, K.; Vilaivan, T. "Synthesis of aryl esters of protected amino acids from aryl sulfonates" Tetrahedron Lett. 1999, 40(32), 5939–5942.

13.    Lowe, G.; Droz, A.S.; Vilaivan, T.; Weaver, G.W.; Park, J.J.; Pratt, J.M. Tweedale, L.; Kelland, L.R. "Cytotoxicity of (2,2':6',2"-terpyridine)platinum(II) complexes against Human Ovarian Carcinoma" J. Med. Chem. 1999, 42, 3167–3174.

14.    Sithigorngul, P.; Panchan, N.; Vilaivan, T.; Sithigorngul, W.; Petsom, A. "Immunochemical analysis and immunocytochemical localization of crustacean hyperglycemic hormone from the eyestalk of Macrobrachium rosenbergii" Comp. Biochem. Phys. B 1999, 124(1), 73–80.

15.    Rastelli, G.; Sirawaraporn, W.; Sompornpisut, P.; Vilaivan, T.; Kamchonwongpaisan, S.; Quarrell, R.; Lowe, G.; Thebtaranonth, Y.; Yuthavong, Y. "Interaction of pyrimethamine, cycloguanil, WR99210 and their analogues with Plasmodium falciparum dihydrofolate reductase: Structural basis of antifolate resistance" Bioorg. Med. Chem. 2000, 8, 1117–1128.

16.    Yuthavong, Y.; Vilaivan, T.; Chareonsethakul, N.; Kamchonwongpaisan, S.; Sirawaraporn, W.; Quarrell, R.; Lowe, G. "Development of a lead inhibitor for the A16V+S108T mutant of dihydrofolate reductase from the cycloguanil resistant strain (T9/94) of Plasmodium falciparum" J. Med. Chem. 2000, 43, 2738–2744.

17.    Vilaivan, T.; Khongdeesameor, C.; Harnyuttanakorn, P.; Westwell, M.S.; Lowe, G. "Synthesis and properties of chiral peptide nucleic acids with a N-aminoethyl-D-proline backbone" Bioorg. Med. Chem. Lett. 2000, 10(22), 2541–2545.

18.    Roengsumran, S.; Petsom, A.; Kuptiyanuwat, N.; Vilaivan, T.; Ngamrojnavanich, N.; Chaichantipyuth, C.; Phuthong, S. "Cytotoxic labdane diterpenoids from Croton oblongifolius" Phytochemistry 2001, 56(1), 103–107.

19.    Pudhom, K.; Vilaivan, T. "Pentafluorophenyl 4-nitrobenzenesulfonate as a peptide coupling reagent" Synth. Commun. 2001, 31(1), 61–70.

20.    Vilaivan, T.; Khongdeesameor, C.; Wiriyawaree, W.; Mansawat, W.; Westwell, M.S.; Lowe, G. "Synthesis and properties of novel peptide nucleic acids with hydrophilic serine spacers" Science Asia 2001, 27(2), 113–120.

21.    Vilaivan, T.; Suparpprom, C.; Harnyuttanakorn, P.; Lowe, G. "Synthesis and properties of novel pyrrolidinyl PNA carrying beta-amino acid spacers", Tetrahedron Lett. 2001, 42(32), 5533-5536.

22.    Suparpprom, C.; Vilaivan, T. "Synthesis of 2-[4'-(ethylcarbamoyl)phenyl]-N-acetylglycine, the proposed structure for giganticine" J. Nat. Prod. 2001, 64(8), 1114–1116.

23.    Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. "Indium mediated Barbier-type allylation of aldimines in alcoholic solvents" Tetrahedron Lett. 2001, 42(51), 9073–9076.

24.    Roengsumran, S.; Musikul, K.; Petsom, A.; Vilaivan, T.; Sangvanich, P. ; Pornpakakul, S.; Puthong, S.; Chaichantipyuth, C.; Jaiboon, N.; Chaichit, N. "Croblongifolin, a new anticancer clerodane from Croton oblongifolius", Planta Med. 2002, 68(3), 274–277.

25.    Saesaengseerung, N.; Vilaivan, T.; Thebtaranonth, Y. "An efficient synthesis of 1-aryl-4,6-diamino-1,2-dihydro- 1,3,5-triazines" Synth. Commun. 2002, 32(14), 2089–2100.

26.    Vilaivan, T.; Lowe, G. "A novel pyrrolidinyl PNA showing high sequence specificity and preferential binding to DNA over RNA" J. Am. Chem. Soc. 2002, 124(32), 9326–9327.

27.    Vilaivan, T.;  Saesaengseerung, N.; Jarprung, D; Kamchonwongpaisan, S.; Sirawaraporn, W.; Yuthavong, Y. "Synthesis of solution-phase combinatorial library of 4,6-diamino-1,2-dihydro-1,3,5-triazine and identification of new leads against A16V+S108T mutant dihydrofolate reductase of Plasmodium falciparum" Bioorg. Med. Chem. 2003, 11(2), 217–224.

28.    Vilaivan, T.; Suparpprom, C.; Duanglaor, P.; Harnyuttanakorn, P.; Lowe, G. "Synthesis and nucleic acid binding studies of novel pyrrolidinyl PNA carrying an N-amino-N-methylglycine spacer" Tetrahedron Lett. 2003, 44(8), 1663–1666.

29.    Mansawat, W.; Bhanthumnavin, W.; Vilaivan, T. "N-Salicyl-beta-aminoalcohols as a new class of ligand for catalytic asymmetric Strecker reactions" Tetrahedron Lett. 2003, 44(19), 3805–3808.

30.    Janwitayanuchit, W; Suwanborirux, K.; Patarapanich, C.; Pummangura, S.; Lipipun, V.; Vilaivan, T. "Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides" Phytochemistry 2003, 64, 1253–1264.

31.    Kamchonwongpaisan, S.; Quarrell, R.; Charoensethakul, N.; Ponsinet, R.; Vilaivan, T.; Vanichtanankul, J.; Tarnchompoo, B.; Sirawaraporn, W.; Lowe, G.; Yutavong, Y. "Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities" J. Med. Chem. 2004, 47, 673–680.

32.    Banphavichit, V.; Chaleawlertumpon, S.; Bhanthumnavin, W.; Vilaivan, T. "A convenient synthesis of N-Boc-protected alpha-aminonitriles from alpha-amidosulfones" Synth. Commun. 2004, 34(17), 3147–3160.

33.    Banphavichit, V.; Mansawat, W.; Bhanthumnavin, W.; Vilaivan, T. "A highly enantioselective Strecker reaction catalyzed by titanium-N-salicyl-beta-aminoalcohol complexes" Tetrahedron 2004, 60(46), 10559–10568. (Tetrahedron Symposia-in-Print: Synthesis and Applications of Non-Racemic Cyanohydrins and alpha-Amino Nitriles)

34.    Yuthavong, Y.; Yuvaniyama, J.; Chitnumsub, P.;  Vanichtanankul, J.; Chusacultanachai, S.; Tarnchompoo, B.; Vilaivan, T.; Kamchonwongpaisan, S. "Malarial (Plasmodium falciparum) dihydrofolate reductase-thymidylate synthase: structural basis for antifolate resistance and development of effective inhibitors" Parasitology 2005, 130, 249–259.

35.    Suparpprom, C.; Srisuwannaket, C.; Sangvanich, P.; Vilaivan, T. "Synthesis and oligodeoxynucleotide binding properties of pyrrolidinyl peptide nucleic acids bearing prolyl-2-aminocyclopentanecarboxylic acid (ACPC) backbones" Tetrahedron Lett.  2005, 46(16), 2833–2837.

36.    Vilaivan, T.; Winotapan, C.; Banphavichit, V.; Shinada, T.; Ohfune, Y. "Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: Synthesis of optically active homoallylic amines" J. Org. Chem. 2005, 70(9), 3464–3471.

37.    Vilaivan, T.; Bhanthumnavin, W.; Sritana-Anant, Y. "Recent advances in catalytic asymmetric addition to imines and related C=N systems" Curr. Org. Chem. 2005, 9(14), 1315–1392.

38.    Vilaivan, T.; Srisuwannaket, C. "Hybridization of pyrrolidinyl peptide nucleic acids and DNA: Selectivity, base-pairing specificity, and direction of binding" Org. Lett. 2006, 8(9), 1897–1900.

39.    Ananthanawat, C.; Banphavichit, V.; Vilaivan, T. "Convenient procedure for synthesis of N-protected beta-aminomalonates and beta-amino acids from alpha-amidosulfones" Synth. Commun. 2006, 36(13), 1845–1855.

40.    Vilaivan, T. "A rate enhancement of tert-butoxycarbonylation of aromatic amines with Boc2O in alcoholic solvents" Tetrahedron Lett. 2006, 47(38), 6739–6742.

41.    Pudhom, K.; Vilaivan, T.; Ngamrojanavanich, N.; Dechangvipart, S.; Sommit, D.; Petsom, A.; Roengsumran, S." Furanocembranoids from the stem bark of Croton oblongifolius"  J. Nat. Prod. 2007, 70(4), 659–661.

42.    Mansawat, W.; Saengswang, I.; U-prasitwong, P.; Bhanthumnavin, W.; Vilaivan, T. "Novel thiolated amino-alcohols as chiral ligands for copper-catalyzed asymmetric nitro-aldol reactions" Tetrahedron Lett. 2007, 48(24), 4235–4238.

43.    Banphavichit, V.; Bhanthumnavin, W.; Vilaivan, T. "Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction" Tetrahedron 2007, 63(36), 8727–8734.

44.    Sathapornvajana, S.; Vilaivan, T. "Prolinamides derived from aminophenols as organocatalysts for asymmetric direct aldol reactions" Tetrahedron 2007, 63(41), 10253–10259.

45.    Siriwong, K.; Chuichay, P.; Saen-oon, S.; Suparpprom, C.; Vilaivan, T.; Hannongbua, S. "Insight into why pyrrolidinyl peptide nucleic acid binding to DNA is more stable than the DNA•DNA duplex" Biochem. Biophys. Res. Commun. 2008, 372, 765–771.

46.    Boontha B.; Nakkuntod, J.; Hirankarn, N.; Chaumpluk, P.;Vilaivan, T. "Multiplex mass spectrometric genotyping of single nucleotide polymorphisms employing pyrrolidinyl peptide nucleic acid in combination with ion-exchange capture" Anal. Chem. 2008, 80(21), 8178–8186.

47.    Ananthanawat, C.; Vilaivan, T.; Hoven, V.P. "Synthesis and immobilization of thiolated pyrrolidinyl peptide nucleic acids on gold-coated piezoelectric quartz crystals for the detection of DNA hybridization" Sens. Actuators B: Chem. 2009, 137(1), 215–221.

48.    Maitarad, P.; Kamchonwongpaisan, S.; Vanichtanankul, J.; Vilaivan, T.; Yuthavong, Y.; Hannongbua, S. "Interactions between cycloguanil derivatives and wild type and resistance-associated mutant Plasmodium falciparum dihydrofolate reductases" J. Comput. Aided Mol. Des. 2009, 23, 241–252.

49.    Banphavichit, V.; Mansawat, W.; Bhanthumnavin, W.; Vilaivan, T. "A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction" Tetrahedron 2009, 65, 5849–5854.

50.    Ananthanawat, C.; Vilaivan, T.; Mekboonsonglarp, W.; Hoven, V. P. "Thiolated pyrrolidinyl peptide nucleic acids for the detection of DNA hybridization using surface plasmon resonance" Biosens. Bioelectron. 2009, 24, 3544–3549.

51.    Chitnumsub, P.; Yuvaniyama,J.; Chahomchuen, T.; Vilaivan, T.;  Yuthavong, Y. "Crystallization and preliminary crystallographic studies of dihydrofolate reductase-thymidylate synthase from Trypanosoma cruzi, the Chagas disease pathogen" Acta Cryst. 2009, F65, 1175–1178.

52.    Ananthanawat, C.; Vilaivan, T.; Hoven, V. P.; Su, X. "Comparison of DNA, aminoethylglycyl PNA and pyrrolidinyl PNA as probes for detection of DNA hybridization using surface plasmon resonance technique" Biosens. Bioelectron. 2010, 25, 1064–1069.

53.    Nuanyai, T.; Chokpaiboon, S.; Vilaivan, T.; Pudhom, K. "Cytotoxic 3,4-seco-cycloartane triterpenes from the exudate of Gardenia tubifera" J. Nat. Prod. 2010, 73, 51–54.

54.    Vilaivan, T.; Bhanthumnavin, W. "Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds" Molecules 2010, 15, 917–958.

55.    Taechalertpaisarn, J.; Sriwarom, P.; Boonlua, C.; Yotapan, N.; Vilaivan, C.; Vilaivan, T. "DNA-, RNA- and self-pairing properties of a pyrrolidinyl peptide nucleic acid with a (2’R,4’S)-prolyl-(1S,2S)-2-aminocyclopentanecarboxylic acid backbone" Tetrahedron Lett 2010, 51, 5822–5826.

56.    Ananthanawat, C.; Hoven, V. P.; Vilaivan, T.; Su, X. "Surface plasmon resonance study of PNA interactions with double-stranded DNA " Biosens. Bioelectron. 2011, 26, 1918–1923.

57.    Ngamwiriyawong, P. Vilaivan, T. "Synthesis and nucleic acids binding properties of diastereomeric aminoethylprolyl peptide nucleic acids (aepPNA)" Nucleosides Nucleotides and Nucleic Acids 2011, 30, 97–112.

58.    Nuanyai T., Sappapan R., Vilaivan T., Pudhom, K. "Gardenoins E-H, Cycloartane triterpenes from the apical buds of Gardenia obtusifolia" Chem. Pharm. Bull. 2011, 59, 385–387.

59.    Nuanyai T., Sappapan R., Vilaivan T., Pudhom, K. "Cycloartane triterpenes from the exudate of Gardenia thailandica" Phytochemistry Lett. 2011, 4, 26–29.

60.    Nuanyai T., Sappapan R., Vilaivan T., Pudhom, K. "Dammarane triterpenes from the apical buds of Gardenia collinsae" Phytochemistry Lett. 2011, 4, 183–186.

61.    Vilaivan, C.; Srisuwannaket, C.; Ananthanawat, C.; Suparpprom, C.; Kawakami, J.; Yamaguchi, Y.; Tanaka, Y.; Vilaivan, T. "Pyrrolidinyl peptide nucleic acid with alpha/beta-peptide backbone: A conformationally constrained PNA with unusual hybridization properties" Artificial DNA: PNA & XNA 2011, 2, 50–59.

62.    Sangthong, S.; Krusong, K.; Ngamrojanavanich, N.; Vilaivan, T.; Puthong, S.; Chandchawan, S.; Muangsin, N. "Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities" Bioorg. Med. Chem. Lett. 2011, 21, 4813–4818.

63.    Vanichtanankul, J.; Taweechai, S.; Yuvaniyama, J.; Vilaivan, T.;  Chitnumsub, P.; Kamchonwongpaisan, S.; Yuthavong, Y. "Trypanosomal dihydrofolate reductase reveals natural antifolate resistance" ACS Chem. Biol. 2011, 6, 905–911.

64.    Reenabthue, N.; Boonlua, C.; Vilaivan C.; Vilaivan, T.; Suparpprom, C. "3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA" Bioorg. Med. Chem. Lett. 2011, 21, 6465–6469.

65.    Boonlua, C.; Vilaivan, C.; Wagenknecht, H.-A.; Vilaivan, T. "5-(Pyren-1-yl)uracil as a base-discriminating fluorescent nucleobase in pyrrolidinyl peptide nucleic acids" Chem. Asian J. 2011, 6, 3251–3259.

66.    Rutnakornpituk, B.; Wichai, U.; Vilaivan, T.; Rutnakornpituk, M. "Surface-initiated atom transfer radical polymerization of poly(4-vinylpyridine) from magnetite nanoparticle" J. Nanopart. Res. 2011, 13, 6847–6857.

67.    Pudhom, K.; Nuanyai, T.; Matsubara, K.; Vilaivan, T. "Antiangiogenic activity of 3,4-seco-cycloartane triterpenes from Thai Gardenia spp. and their semi-synthetic analogs" Bioorg. Med. Chem. Lett. 2012, 22, 512–517.

68.    Rashatasakhon, P.; Vongnam, K.; Siripornnoppakhun, W.; Vilaivan, T.; Sukwattanasinitt, M. "FRET detection of DNA sequence via electrostatic interaction of polycationic phenyleneethynylene dendrimer with DNA/PNA hybrid" Talanta 2012, 88, 593–598.

69.    Yuanboonlim, W.; Siripornnoppakhun, W.; Niamnont, N.; Rashatasakhon, P.; Vilaivan, T.; Sukwattanasinitt, M. "Phenylene–ethynylene trication as an efficient fluorescent signal transducer in an aptasensor for potassium ion" Biosens. Bioelectron. 2012, 33, 1918–1923.

70.    Virakul, S.; Kupatawintu, P.; Nakkuntod, J.; Kangwanshiratada, O.; Vilaivan, T.; Hirankarn, N. "A nested sequence-specific primer-polymerase chain reaction for the detection of HLA-B*15:02" Tissue Antigens 2012, 79(4), 295–301.