Publications by J.L. Giner


1.           Cohen, S.G.; Elkind, J.L.; Chishti, S.B.; Giner, J.-L.P.; Reese, H.; Cohen, J.B., "Effects of Volume and Surface Property in Hydrolysis by Acetylcholinesterase. The Trimethyl Site", J. Med. Chem. 1984, 27,1643-1647.

2.           Giner, J.-L.; Zimmerman, M.P.; Djerassi, C., "Synthesis of (24R,28R)- and (24S,28S)-24,28-Methylene-5-stigmasten-3β-ol and Biosynthetic Implications of Cyclopropyl Cleavage to 24-Substituted Cholesterols", J. Org. Chem. 1988, 53, 5895-5902.

3.           Hensens, O.D.; Giner, J.-L.; Goldberg, I.H., "Biosynthesis of NCS Chrom A, the Chromophore of the Antitumor Antibiotic Neocarzinostatin", J. Am. Chem. Soc. 1989, 111,3295-3299.

4.           Giner, J.-L.; Margot, C.; Djerassi, C., "Scope and Regiochemical Control of the Allylpotassium Reaction in the Synthesis of Sterols with Unsaturated Side Chains", J. Org. Chem. 1989, 54, 2117-2125.

5.           Giner, J.-L.; Margot, C.; Djerassi, C., "Stereospecificity and Regiospecificity of the Phosphorus Oxychloride Dehydration of Sterol Side Chain Alcohols", J. Org. Chem. 1989, 54, 369-373.

6.           Giner, J.-L.; Djerassi, C., "Use of Sponge Cell-Free Extracts in the Study of Marine Sterol Biosynthesis", Tetrahedron Lett. 1990, 31, 5421-5424.

7.           Giner, J.-L.; Djerassi, C., "Inhibition and Substrate Specificity of Yeast Δ22 -Desaturase", Biochem. Biophys. Res. Commun. 1990, 173, 60-66.

8.           Giner, J.-L.; Silva, C.J.; Djerassi, C., "The Missing Step in Sterol Cyclopropyl Biosynthesis: Enzymatic Desaturation of 24(S)-Ethylcholesterol", J. Am. Chem. Soc. 1990, 112,9626-9627.

9.           Giner, J.-L.; Djerassi, C., "Biosynthesis of 24-Methylene-25-methylcholesterol in Phaseolus Vulgaris", Phytochemistry 1991, 30, 811-814.

10.           Giner, J.-L.; Djerassi, C., "Evidence for a Protonated Cyclopropyl Intermediate in the Biosynthesis of 24-Propylidenecholesterol", J. Am. Chem. Soc. 1991, 113, 1386-1393.

11.           Giner, J.-L.; Djerassi, C., "Biosynthesis of Dinosterol, Peridinosterol, and Gorgosterol: Unusual Patterns of Bioalkylation in Dinoflagellate Sterols", J. Org. Chem. 1991, 56, 2357-2363.

12.           Giner, J.-L.; Wünsche, L.; Andersen, R.A.; Djerassi, C., "Dinoflagellates Cyclize Squalene Oxide to Lanosterol", Biochem. Syst. Ecol. 1991, 19, 142-145.

13.           Giner, J.-L.; Djerassi, C., "Generation of the Cyclopropane Ring of Sormosterol", Acta Chem. Scand. 1992, 46, 678-679.

14.           Silva, C.J.; Giner, J.-L.; Djerassi, C., "Enzymatic Desaturation of 24(S)-Methylcholesterol to 23,24-Methylenecholesterol, Norficisterol, and Norhebesterol. Further Evidence for a Unified Biosynthesis of Marine Sterols with Unique Side Chains", J. Am. Chem. Soc. 1992, 114, 295-299.

15.           Giner, J.-L.; Djerassi, C., "23-Epidihydrocalysterol: A New Cyclopropane-Containing Sponge Sterol", Steroids, 1992, 57, 258-261.

16.           Giner, J.-L.; Djerassi, C., "Evidence for Sterol Side Chain Dealkylation in an Alga", Phytochemistry 1992, 31, 3865-3867.

17.           Giner, J.-L., "Biosynthesis of Marine Sterol Side Chains", Chem. Rev. 1993, 93, 1735-1752.

18.           Giner, J.-L.; Rando, R.R., "A Novel Methyltranferase Activity Modifying the Carboxy Terminal bis(Geranylgeranyl)-Cys-Ala-Cys Structure of Small GTP-Binding Proteins", Biochemistry 1994, 33, 15116-15123.

19.           Giner, J.-L.; Hormann, R.; Arigoni, D. "Multiply Labelled Substrates as Tools for the Study of an Unusual Biomethylation Reaction", In "Proceedings of the 5th International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds 1994, Strasbourg, France", Allen, J. and Voges, R., Eds., John Wiley & Sons, London, 1995, pp. 723-726.

20.           Giner, J.-L.; Djerassi, C., "A Reinvestigation of the Biosynthesis of Lanosterol in Euphorbia lathyris", Phytochemistry 1995, 39, 333-335.

21.           Giner, J.-L.; Buzek, P.; Schleyer, P. v. R., "The Mechanism of Cyclopropane-Cyclopropane Rearrangements in Marine Sterol Biosynthesis: Ab Initio Calculations on Protonated Ethylcyclopropane", J. Am. Chem. Soc. 1995, 117, 12871-12872.

22.           Marom, M.; Parish, C. A.; Giner, J.-L.; Rando, R.R., "Minimal Structural Requirements for Diglyceride-Site Directed Activators of Protein Kinase C", Tetrahedron 1997, 29, 10041-10050.

23.           Giner, J.-L.; Boyer, G.L., "Sterols of the Brown Tide Alga Aureococcus anophagefferens", Phytochemistry 1998, 48, 475-477.

24.           Giner, J.L., "New and Efficient Synthetic Routes to 1-Deoxy-D-xylulose", Tetrahedron Lett. 1998, 39, 2479-2482.

25.           Giner, J.-L.; Jaun, B.; Arigoni, D., "Biosynthesis of Isoprenoids in Escherichia coli: The Fate of the 3-H and 4-H Atoms of 1-Deoxy-D-xylulose", J. Chem. Soc., Chem. Commun. 1998, 1857-1858.

26.            Giner, J.-L.; Jaun, B., "Biosynthesis of Isoprenoids in Escherichia coli: Retention of the Methyl H-Atoms of 1-Deoxy-D-Xylulose", Tetrahedron Lett. 1998, 39, 8021-8022.

27.            Arigoni, D., Giner, J.-L.; Sagner, S., Wungsintaweekul, J., Zenk, M.H., Kis, K., Bacher, A., Eisenreich, W., "Stereochemical Course of the Reduction Step in the Formation of 2-C-Methyl-Erythritol From the Terpene Precursor 1-Deoxyxylulose in Higher Plants", J. Chem. Soc., Chem. Commun. 1999, 1127-1128.

28.           Giner, J.-L.; Gunasekera, S.P.; Pomponi, S.A., "Sterols from the Marine Sponge Petrosia Weinbergii: Implications for the Absolute Configuration of the Antiviral Weinbersterols and Orthoesterols", Steroids 1999, 64, 820-824..

29.           Giner, J.-L.; Berkowitz, J.D.; Andersson, T., "Nonpolar Components of the Latex of Euphorbia peplus", J. Nat. Prod. 2000, 63, 267-269.

30.            Lovato, M.A.; Hart, E.A.; Segura, M.J.R.; Giner, J.-L.; Matsuda, S.P.T., "Functional Cloning of an Arabidopsis thaliana cDNA Encoding Cyclopropyl Isomerase", J. Biol. Chem. 2000, 275, 13394-13397.

31.           Giner, J.-L.; Li, X., "Stereospecific Synthesis of 24-Propylcholesterol Isolated from the Texas Brown Tide", Tetrahedron 2000, 56, 9575-9580.

32.           Giner, J.-L.; Li, X.; Boyer, G.L., "Sterol Composition of Aureoumbra lagunensis, the Texas Brown Tide Alga", Phytochemistry 2001, 57, 787-789.

33.           Giner, J.-L.; Beach, D.H.; Parish, E.J.; Jayasimhulu, K.; Kaneshiro, E.S., "Definitive structural identities of 42 sterol components in Pneumocystis carinii", J. Eukaryot. Microbiol. 2001, 48, 142S-143S.

34.           Kaneshiro, E.S.; Rosenfeld, J.A.; Basselin, M.; Bradshaw, S.; Stringer, J.R.; Smulian, A.G.; Giner, J.-L., "Pneumocystis carinii erg6 gene: sequencing and expression of recombinant SAM:sterol methyltransferase in heterologous systems", J. Eukaryot. Microbiol. 2001, 48, 144S-146S.

35.           Giner, J.-L.; Zhao, H.; Beach, D.H.; Parish, E.J.; Jayasimhulu, K.; Kaneshiro, E.S., "Comprehensive and definitive structural identities of Pneumocystis carinii sterols", J. Lipid Res. 2002, 43, 1114-1124.

36.           Kaneshiro, E.S.; Rosenfeld, J.A.; Basselin-Eiweida, M.; Bradshaw, S.; Stringer, J.R.; Smulian, A.G.; Giner, J.-L., "The Pneumocystis carinii drug target S-adenosyl-L-methionine:sterol C-24 methyl transferase has a unique substrate preference", Mol. Microbiol. 2002, 44, 989-999.

37.           Giner, J.-L.; Kiemle, D.; Zuniga, D.J., "Analysis of 2-Deuterated Isopentenyl Alcohols by 1H-NMR of Chiral Esters", Tetrahedron Lett. 2002, 43, 1175-1177.

38.           Giner, J.-L.; Faraldos, J.A., "A Biomimetic Approach to the Synthesis of an Antiviral Marine Steroidal Orthoester", J. Org. Chem. 2002, 67, 2717-2720.

39.           Giner, J.-L.; Faraldos, J.A., "A Biomimetic Synthesis of Petuniasterone D via the Epoxy Ester - Orthoester Rearrangement", J. Org. Chem. 2002, 67, 4659-4666.

40.           Giner, J.-L.; William V. Ferris, J., "Synthesis of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate", Org. Lett. 2002, 4, 1225-1226

41.            Giner, J.-L.; William V. Ferris, J.; Mullins, J.J., "Synthesis of 2-Methyl-D-erythritol via Epoxy Ester-Orthoester Rearrangement", J. Org. Chem. 2002, 67, 4856-4859.

42.           Giner, J.-L.; Arigoni, D., "Enantiomerically Enriched [2-2H]-Isopentenyl Alcohol from (E)-2-Methyl-2-butene-1,4-diol by an Asymmetric Retro-Ene Reaction", Chem. Commun. 2002, 1388-1389.

43.           Giner, J.-L., "A Convenient Synthesis of (E)-4-Hydroxy-3-methyl-2-butenyl Pyrophosphate and its [4-13C]-Labeled Form", Tetrahedron Lett. 2002, 43, 5457-5459.

44.           Giner, J.-L.; Faraldo, J.A.; Boyer, G.L., "Unique Sterols of the Toxic Dinoflagellate Gymnodinium breve (Dinophyceae): A Defensive Function for Unusual Marine Sterols?", J. Phycol. 2003, 39, 315-319.

45.           Crowell, D.N.; Packard, C.E.; Pierson, C.A.; Jose-Luis, G.; Downes, B.P.; Chary, S.N., "Identification of an Allele of CLA1 Associated with Variegation in Arabidopsis thaliana", Physiol. Plant. 2003, 118, 29-37.

46.           Giner, J.-L.; Faraldos, J.A., "Facile Orthoester Formation in a Model Compound of the Taxol Oxetane: Are Biologically Active Epoxy Esters, Orthoesters and Oxetanyl Esters Latent Electrophiles?", Helv. Chim. Acta 2003, 86, 3613-3622.

47.           Giner, J.-L.; Li, X.; Mullins, J.J., "Mechanistic Studies of the Biomimetic Epoxy Ester - Orthoester and Orthoester - Cyclic Ether Rearrangements", J. Org. Chem. 2003, 68, 10079-10086.

48.           Zhao, H.; Giner, J.-L.; Kaneshiro, E.S., "Definitive structural identities of Pneumocystis jirovecii sterols", J. Eukaryot. Microbiol. 2003, 50, 680.

49.           Giner, J.-L.; Zhao, H.; Amit, Z.; Kaneshiro, E. S.,Sterol composition of Pneumocystis jirovecii with blocked 14a-demethylase activity, J. Eukaryot. Microbiol. 2004, 51, 634-643.

50.           Giner, J.-L.; Zhao, H.,Detailed Sterol Compositions of Two Pathogenic Rust Fungi, Lipids 2004, 39, 763-767.

51.           Giner, J.-L., DMOBO: An Improvement on the OBO Orthoester Protecting Group, Org. Lett. 2005, 7, 499-501.

52..            Giner, J.-L.,Tetrahydropyran Formation by Rearrangement of an Epoxy Ester: A Model for the Biosynthesis of Marine Polyether Toxins, J. Org. Chem. 2005, 70, 721-724.

53.           Giner, J.-L.; Rocchetti, S.; Neunlist, S.; Rohmer, M.; Arigoni, D.,"Detection of 1,2-hydride shifts in the formation of euph-7-ene by the squalene-tetrahymanol cyclase of Tetrahymena pyriformis", Chem. Commun. 2005, 3089-3091.

54.           Müller-Schwarze, D.; Giner, J., Cottontails and Gopherweed: Anti-Feeding Compounds from a Spurge. In Chemical Signals in Vertebrates, Mason, R. T.; LeMaster, M. P.; Müller-Schwarze, D., Eds. Springer: New York, NY, 2005; Vol. 10, pp 409-416.

55.           Giner, J.-L.; Zhao, H., "A convenient method for the preparation of Δ4,7-steroidal 3-ketones and Δ5,7 sterols", Polish J. Chem. 2006, 80, 605-609.

56.           Giner, J.-L.; Kehbein, K. A.; Cook, J. A.; Smith, M. C.; Vlahos, C. J.; Badwey, J. A., "Synthesis of fluorescent derivatives of wortmannin and demethoxyviridin as probes for phosphatidylinositol 3-kinase", Bioorg. Med. Chem. Lett. 2006, 16, 2518-2521.

57.           Jayasimhulu, K.; Hunt, S. M.; Kaneshiro, E. S.; Watanabe, Y.; Giner, J.-L.,"Detection and Identification of Bacteriovorax stolpii UKi2 Sphingophosphonolipid Molecular Species", J. Am. Soc. Mass Spectrom. 2007, 18, 394-403.

58.           Giner, J.-L.; Kiemle, D. J.; Kutrzeba, L.; Zjawiony, J.,"Unambiguous NMR spectral assignments of salvinorin A", Mag. Reson. Chem. 2007, 45, 351-354.

59.           Giner, J.-L.,"Marine Natural Products”. Topics in Heterocyclic Chemistry, 05 edited by Hiromasa Kiyota", J. Am. Chem. Soc. 2007, 129, 4854-4855.

60.           Puan, K.-J.; Jin, C.; Wang, H.; Sarikonda, G.; Raker Amy, M.; Lee Hoi, K.; Samuelson Megan, I.; Marker-Hermann, E.; Pasa-Tolic, L.; Nieves, E.; Giner, J.-L.; Kuzuyama, T.; Morita Craig, T.,"Preferential recognition of a microbial metabolite by human Vγ2Vδ2 T cells", Int. Immunol. 2007, 19, 657-673.

61.           Kutrzeba, L.; Dayan, F. E.; Howell, J. L.; Feng, J.; Giner, J.-L.; Zjawiony, J. K.,"Biosynthesis of salvinorin A proceeds via the deoxyxylulose phosphate pathway", Phytochemistry 2007, 68, 1872-1881.

62.           Giner, J.-L.; Zhao, H.; Tomas, C.," Sterols and Fatty Acids of Three Harmful Algae Previously Assigned as Chattonella", Phytochemistry 2008, 69, 2167-2171.

63.           Puan, K. J.; Low, J. S. H.; Tan, T. W. K.; Wee, J. T. S.; Tan, E. H.; Fong, K. W.; Chua, E. T.; Jin, C.; Giner, J.-L.; Morita, C. T.; Goh, C. H. K.; Hui, K. M.,"Phenotypic and functional alterations of Vγ2Vδ2 T cell subsets in patients with active nasopharyngeal carcinoma", Cancer Immunol. Immunother. 2009, 58, 1095-1107.

64.           Giner, J.-L.; Zhao, H.; Boyer, G.L., Satchwell, M.F., Andersen, R.A.,"Sterol Chemotaxonomy of Marine Pelagophyte Algae ", Chem. Biodivers. 2009, 6, 1111-1130.

65.           Faraldos, J. A.; Giner, J.-L.; Smith, D. H.; Wilson, M.; Ronhovde, K.; Wilson, E.; Clevette, D.; Holmes, A. E.; Rouhier, K.,"Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry", J. Chem. Educ. 2011, 88, 334-336.

66.           Giner, J.-L.; Wikfors, G.," 'Dinoflagellate Sterols' in Marine Diatoms", Phytochemistry 2011, 72, 1896-1901.

67.           Nkinin S.W.; Stringer. J.R; Keely, S.P.; Setchell, K.D.R,; Giner, J.-L.; and Kaneshiro, E.S., "Pneumocystis carinii Sterol 14α-Demethylase Activity in Saccharomyces cerevisiae erg11 Knockout Mutant: Sterol Biochemistry", J. Eukaryot. Microbiol. 2011, 58, 383-339.

68.            Wang, H.; Sarikonda, G.; Puan, K.-J.; Tanaka, Y.; Feng, J.; Giner, J.-L.; Cao, R.; Mönkkönen, J.; Oldfield, E.; Morita, C. T.,"Indirect Stimulation of Human Vγ2Vδ2 T Cells Through Alterations in Isoprenoid Metabolism", J. Immunol. 2011, 187, 5099-5113.

69.            Giner, J.-L.; Wang, H.; Morita, C. T.,"Synthesis and immunological evaluation of the 4-b-glucoside of HMBPP", Bioorg. Med. Chem. Letters 2012, 22, 811-813.

70.            Hong, Y. J.; Giner, J.-L.; Tantillo, D. J.,"Triple Shifts and Thioether Assistance in Rearrangements Associated with an Unusual Biomethylation of the Sterol Side Chain", J. Org. Chem. 2013, 78, 935–941.

71.            Sallans, L.; Giner, J.-L.; Kiemle, D. J.; Custer, J. E.; Kaneshiro, E. S.,"Structural identities of four glycosylated lipids in the oral bacterium Streptococcus mutans UA159", Biochim. Biophys. Acta 2013, 1831, 1239-1249.

 72.            Grabenstatter, J.; Méhay, S.; McIntyre-Wressnig, A.; Giner, J.-L.; Edgcomb, V. P.; Beaudoin, D. J.; Bernhard, J. M.; Summons, R. E.,"Identification of 24-n-propylidenecholesterol in a member of the Foraminifera", Org. Geochem. 2013, 63, 145-151.

73.            Faraldos, J. A.; Coates, R. M.; Giner, J.-L.,"Alternative Synthesis of the Colorado Potato Beetle Pheromone", J. Org. Chem. 2013, 78, 10548-10554.

74.       Giner, J.-L.; Joseph, R.; Berry, D.; Ceballos, H.; Wikfors, G. H.; Hassett, R. P.,"Diving Deeper with Marine Sterols", Chem. Listy 2014, 108, 1092.

75.       Hong, Y. J.; Giner, J.-L.; Tantillo, D. J.,"Bicyclobutonium ions in biosynthesis - Interconversion of cyclopropyl-containing sterols from orchids", J. Am. Chem. Soc. 2015, 137, 2085-2088.

76.       Kaneshiro, E. S.; Johnston, L. Q.; Nkinin, S. W.; Romero, B. I.; Giner, J.-L.,"Sterols of Saccharomyces cerevisiae erg6 Knockout Mutant Expressing the Pneumocystis carinii S-Adenosylmethionine:Sterol C-24 Methyltransferase (SAM:SMT)", J. Eukaryotic Microbiol. 2015, 62, 298-306.

77.       Giner, J.-L.; Schroeder, T. N.,"Polygonifoliol, a New Tirucallane Triterpene from the Latex of the Seaside Sandmat Euphorbia polygonifolia", Chem. Biodivers.  2015, 12, 1126-1129.

78.       Giner, J.-L.; Zhao, H.; Dixon, M. S.; Wikfors, G. H.,"Bioconversion of 13C-labeled microalgal phytosterols to cholesterol by the Northern Bay scallop, Argopecten irradians irradians", Comp. Biochem. Physiol., Part B: Biochem. Mol. Biol. 2016, 192, 1-8.

79.       Giner, J.-L.; Ceballos, H.; Tang, Y.-Z.; Gobler, C. J.," Sterols and Fatty Acids of the Harmful Dinoflagellate Cochlodinium polykrikoides", Chem. Biodivers.  2016, 13, 249-252.

80. Giner, J.-L.; Feng, J.; Kiemle, D. J.,"NMR Tube Degradation Method for Sugar Analysis of Glycosides", J. Nat. Prod. 2016, 79, 2413-2417.

81. Sasse, J.; Schlegel, M.; Borghi, L.; Ullrich, F.; Lee, M.; Liu, G.-W.; Giner, J.-L.; Kayser, O.; Bigler, L.; Martinoia, E.; Kretzschmar, T.,"Petunia hybrida PDR2 is involved in herbivore defense by controlling steroidal contents in trichomes ", Plant, Cell Environ. 2016, 39, 2725–2739.

82. Banta, A. B.; Wei, J. H.; Gill, C. C. C.; Giner, J.-L.; Welander, P. V.,"Synthesis of novel arborane triterpenols by a bacterial oxidosqualene cyclase", Proc. Natl. Acad. Sci. U. S. A. 2017, 114, 245–250.

83. Giner, J.-L.; Feng, J.,"Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis", Org. Biomol. Chem. 2017, 15, 2823 -2830.

84. Ciulla, D.; Jorgensen, M.; Giner, J.-L.; Callahan, B.,"Rescue of a general base mutant in hedgehog protein cholesterolysis using a hyper-nucleophilic substrate", J. Am. Chem. Soc. 2017, 140, 916-918.

85.  Lee, A. K.; Banta, A. B.; Wei, J. H.; Kiemle, D. K.; Feng, J.; Giner, J.-L.; Welander, P. V.,"C-4 sterol demethylation enzymes distinguish bacterial and eukaryotic sterol synthesis", Proc. Natl. Acad. Sci. U. S. A. 2018, 115, 5884-5889.

86. Ciulla, D. A.; Wagner, A. G.; Liu, X.; Cooper, C. L.; Jorgensen, M. T.; Wang, C.; Goyal, P.; Banavali, N. K.; Pezzullo, J. L.; Giner, J.-L.; Callahan, B.,"Sterol A-ring plasticity in hedgehog protein cholesterolysis supports a primitive substrate selectivity mechanism", ChemComm 2019, 54, 1829-1832.

87. Giner, J.-L.,"Batatasenol, a Major Triterpenol from Sweet Potato Skins", Chem. Biodivers. 2019, 16, web before print.