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Items: 1 to 50 of 77

1.

Synthesis of methylerythritol phosphate analogues and their evaluation as alternate substrates for IspDF and IspE from Agrobacterium tumefaciens.

Krasutsky SG, Urbansky M, Davis CE, Lherbet C, Coates RM, Poulter CD.

J Org Chem. 2014 Oct 3;79(19):9170-8. doi: 10.1021/jo501529k. Epub 2014 Sep 23.

2.

Alternative synthesis of the Colorado potato beetle pheromone.

Faraldos JA, Coates RM, Giner JL.

J Org Chem. 2013 Oct 18;78(20):10548-54. doi: 10.1021/jo4017056. Epub 2013 Oct 2.

3.

Formation of the unusual semivolatile diterpene rhizathalene by the Arabidopsis class I terpene synthase TPS08 in the root stele is involved in defense against belowground herbivory.

Vaughan MM, Wang Q, Webster FX, Kiemle D, Hong YJ, Tantillo DJ, Coates RM, Wray AT, Askew W, O'Donnell C, Tokuhisa JG, Tholl D.

Plant Cell. 2013 Mar;25(3):1108-25. doi: 10.1105/tpc.112.100057. Epub 2013 Mar 19.

4.

Dissecting paclitaxel-microtubule association: quantitative assessment of the 2'-OH group.

Sharma S, Lagisetti C, Poliks B, Coates RM, Kingston DG, Bane S.

Biochemistry. 2013 Apr 2;52(13):2328-36. doi: 10.1021/bi400014t. Epub 2013 Mar 19.

5.

Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis.

Yeo YS, Nybo SE, Chittiboyina AG, Weerasooriya AD, Wang YH, Góngora-Castillo E, Vaillancourt B, Buell CR, DellaPenna D, Celiz MD, Jones AD, Wurtele ES, Ransom N, Dudareva N, Shaaban KA, Tibrewal N, Chandra S, Smillie T, Khan IA, Coates RM, Watt DS, Chappell J.

J Biol Chem. 2013 Feb 1;288(5):3163-73. doi: 10.1074/jbc.M112.415836. Epub 2012 Dec 14.

6.

Structure and mechanism of the diterpene cyclase ent-copalyl diphosphate synthase.

Köksal M, Hu H, Coates RM, Peters RJ, Christianson DW.

Nat Chem Biol. 2011 May 22;7(7):431-3. doi: 10.1038/nchembio.578.

7.

2-azapinanes: aza analogues of the enantiomeric pinyl carbocation intermediates in pinene biosynthesis.

Faraldos JA, Kariuki BM, Coates RM.

Org Lett. 2011 Mar 4;13(5):836-9. doi: 10.1021/ol1027893. Epub 2011 Jan 24.

8.

Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis.

Köksal M, Jin Y, Coates RM, Croteau R, Christianson DW.

Nature. 2011 Jan 6;469(7328):116-20. doi: 10.1038/nature09628. Epub 2010 Dec 15.

9.

Characterization of the kaurene oxidase CYP701A3, a multifunctional cytochrome P450 from gibberellin biosynthesis.

Morrone D, Chen X, Coates RM, Peters RJ.

Biochem J. 2010 Nov 1;431(3):337-44. doi: 10.1042/BJ20100597.

PMID:
20698828
10.

Enantioselective inhibition of squalene synthase by aziridine analogues of presqualene diphosphate.

Koohang A, Bailey JL, Coates RM, Erickson HK, Owen D, Poulter CD.

J Org Chem. 2010 Jul 16;75(14):4769-77. doi: 10.1021/jo100718z.

11.

A single residue switch for Mg(2+)-dependent inhibition characterizes plant class II diterpene cyclases from primary and secondary metabolism.

Mann FM, Prisic S, Davenport EK, Determan MK, Coates RM, Peters RJ.

J Biol Chem. 2010 Jul 2;285(27):20558-63. doi: 10.1074/jbc.M110.123307. Epub 2010 Apr 29.

12.

Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.

Faraldos JA, O'Maille PE, Dellas N, Noel JP, Coates RM.

J Am Chem Soc. 2010 Mar 31;132(12):4281-9. doi: 10.1021/ja909886q.

PMID:
20201526
13.

Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates.

Noel JP, Dellas N, Faraldos JA, Zhao M, Hess BA Jr, Smentek L, Coates RM, O'Maille PE.

ACS Chem Biol. 2010 Apr 16;5(4):377-92. doi: 10.1021/cb900295g.

14.

Doubly deuterium-labeled patchouli alcohol from cyclization of singly labeled [2-(2)H(1)]farnesyl diphosphate catalyzed by recombinant patchoulol synthase.

Faraldos JA, Wu S, Chappell J, Coates RM.

J Am Chem Soc. 2010 Mar 10;132(9):2998-3008. doi: 10.1021/ja909251r.

PMID:
20148554
15.
16.

Characterization and inhibition of a class II diterpene cyclase from Mycobacterium tuberculosis: implications for tuberculosis.

Mann FM, Prisic S, Hu H, Xu M, Coates RM, Peters RJ.

J Biol Chem. 2009 Aug 28;284(35):23574-9. doi: 10.1074/jbc.M109.023788. Epub 2009 Jul 2.

17.

Characteristic flavonoids from Acacia burkittii and A. acuminata heartwoods and their differential cytotoxicity to normal and leukemia cells.

Grace MH, Wilsonb GR, Kandil FE, Dimitriadis E, Coates RM.

Nat Prod Commun. 2009 Jan;4(1):69-76.

PMID:
19370878
18.

Specificity of the N-benzoyl transferase responsible for the last step of Taxol biosynthesis.

Long RM, Lagisetti C, Coates RM, Croteau RB.

Arch Biochem Biophys. 2008 Sep 15;477(2):384-9. doi: 10.1016/j.abb.2008.06.021. Epub 2008 Jun 28.

19.

X-ray crystallographic studies of substrate binding to aristolochene synthase suggest a metal ion binding sequence for catalysis.

Shishova EY, Yu F, Miller DJ, Faraldos JA, Zhao Y, Coates RM, Allemann RK, Cane DE, Christianson DW.

J Biol Chem. 2008 May 30;283(22):15431-9. doi: 10.1074/jbc.M800659200. Epub 2008 Apr 2.

20.

The dioxanone approach to (2S,3R)-2-C-methylerythritol 4-phosphate and 2,4-cyclodiphosphate, and various MEP analogues.

Lagisetti C, Urbansky M, Coates RM.

J Org Chem. 2007 Dec 21;72(26):9886-95. Epub 2007 Nov 17.

PMID:
18020362
21.

Inhibition of monoterpene cyclases by inert analogues of geranyl diphosphate and linalyl diphosphate.

Karp F, Zhao Y, Santhamma B, Assink B, Coates RM, Croteau RB.

Arch Biochem Biophys. 2007 Dec 1;468(1):140-6. Epub 2007 Sep 19.

22.

16-Aza-ent-beyerane and 16-Aza-ent-trachylobane: potent mechanism-based inhibitors of recombinant ent-kaurene synthase from Arabidopsis thaliana.

Roy A, Roberts FG, Wilderman PR, Zhou K, Peters RJ, Coates RM.

J Am Chem Soc. 2007 Oct 17;129(41):12453-60. Epub 2007 Sep 25.

24.

Conformational Analysis of (+)-Germacrene A by Variable Temperature NMR and NOE Spectroscopy.

Faraldos JA, Wu S, Chappell J, Coates RM.

Tetrahedron. 2007 Sep 6;63(32):7733-7742.

25.

Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates.

Takahashi S, Yeo YS, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J.

J Biol Chem. 2007 Oct 26;282(43):31744-54. Epub 2007 Aug 22.

26.

Exploring biosynthetic diversity with trichodiene synthase.

Vedula LS, Zhao Y, Coates RM, Koyama T, Cane DE, Christianson DW.

Arch Biochem Biophys. 2007 Oct 15;466(2):260-6. Epub 2007 Jun 28.

27.

Probing the role of the DXDD motif in Class II diterpene cyclases.

Prisic S, Xu J, Coates RM, Peters RJ.

Chembiochem. 2007 May 25;8(8):869-74. No abstract available.

PMID:
17457817
28.

Structure of limonene synthase, a simple model for terpenoid cyclase catalysis.

Hyatt DC, Youn B, Zhao Y, Santhamma B, Coates RM, Croteau RB, Kang C.

Proc Natl Acad Sci U S A. 2007 Mar 27;104(13):5360-5. Epub 2007 Mar 19.

29.

ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia.

Grace MH, Faraldos JA, Lila MA, Coates RM.

Phytochemistry. 2007 Feb;68(4):546-53. Epub 2006 Dec 29.

PMID:
17196627
30.

Functional characterization of the rice kaurene synthase-like gene family.

Xu M, Wilderman PR, Morrone D, Xu J, Roy A, Margis-Pinheiro M, Upadhyaya NM, Coates RM, Peters RJ.

Phytochemistry. 2007 Feb;68(3):312-26. Epub 2006 Dec 1.

PMID:
17141283
31.
32.
33.
34.

Structures, biogenetic relationships, and cytotoxicity of pimarane-derived diterpenes from Petalostigma pubescens.

Grace MH, Jin Y, Wilson GR, Coates RM.

Phytochemistry. 2006 Aug;67(16):1708-15. Epub 2005 Nov 18.

PMID:
16298402
35.

An unexpected diterpene cyclase from rice: functional identification of a stemodene synthase.

Morrone D, Jin Y, Xu M, Choi SY, Coates RM, Peters RJ.

Arch Biochem Biophys. 2006 Apr 15;448(1-2):133-40. Epub 2005 Oct 7.

PMID:
16256063
36.

Surrogate splicing for functional analysis of sesquiterpene synthase genes.

Wu S, Schoenbeck MA, Greenhagen BT, Takahashi S, Lee S, Coates RM, Chappell J.

Plant Physiol. 2005 Jul;138(3):1322-33. Epub 2005 Jun 17.

37.

Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling.

Jin Q, Williams DC, Hezari M, Croteau R, Coates RM.

J Org Chem. 2005 Jun 10;70(12):4667-75.

PMID:
15932303
38.

Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes.

Jin Y, Williams DC, Croteau R, Coates RM.

J Am Chem Soc. 2005 Jun 1;127(21):7834-42.

PMID:
15913373
39.

Molecular recognition of the substrate diphosphate group governs product diversity in trichodiene synthase mutants.

Vedula LS, Rynkiewicz MJ, Pyun HJ, Coates RM, Cane DE, Christianson DW.

Biochemistry. 2005 Apr 26;44(16):6153-63.

PMID:
15835903
40.

Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes.

Takahashi S, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J.

J Biol Chem. 2005 Feb 4;280(5):3686-96. Epub 2004 Nov 2.

41.

Eremophilane sesquiterpenes from capsidiol.

Zhao Y, Schenk DJ, Takahashi S, Chappell J, Coates RM.

J Org Chem. 2004 Oct 29;69(22):7428-35.

PMID:
15497966
42.
44.

Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol.

Urbansky M, Davis CE, Surjan JD, Coates RM.

Org Lett. 2004 Jan 8;6(1):135-8.

PMID:
14703369
45.

Total synthesis of (+/-)-cameroonan-7alpha-ol and biomimetic rearrangements to related nopsane sesquiterpenes.

Davis CE, Duffy BC, Coates RM.

J Org Chem. 2003 Sep 5;68(18):6935-43.

PMID:
12946133
47.

Stereoselective prins cyclizations of delta, epsilon-unsaturated ketones to cis-3-chlorocyclohexanols with TiCl(4).

Davis CE, Coates RM.

Angew Chem Int Ed Engl. 2002 Feb 1;41(3):491-3. No abstract available.

PMID:
12491389
48.

Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase.

Whittington DA, Wise ML, Urbansky M, Coates RM, Croteau RB, Christianson DW.

Proc Natl Acad Sci U S A. 2002 Nov 26;99(24):15375-80. Epub 2002 Nov 13.

49.

Stereospecificity and kinetic mechanism of human prenylcysteine lyase, an unusual thioether oxidase.

Digits JA, Pyun HJ, Coates RM, Casey PJ.

J Biol Chem. 2002 Oct 25;277(43):41086-93. Epub 2002 Aug 16.

50.

Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis.

Wise ML, Urbansky M, Helms GL, Coates RM, Croteau R.

J Am Chem Soc. 2002 Jul 24;124(29):8546-7.

PMID:
12121093

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