{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,10]],"date-time":"2026-03-10T22:32:23Z","timestamp":1773181943439,"version":"3.50.1"},"reference-count":27,"publisher":"Public Library of Science (PLoS)","issue":"8","license":[{"start":{"date-parts":[[2016,8,12]],"date-time":"2016-08-12T00:00:00Z","timestamp":1470960000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["U54 GM-093342"],"award-info":[{"award-number":["U54 GM-093342"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["www.ploscompbiol.org"],"crossmark-restriction":false},"short-container-title":["PLoS Comput Biol"],"DOI":"10.1371\/journal.pcbi.1005053","type":"journal-article","created":{"date-parts":[[2016,8,12]],"date-time":"2016-08-12T17:39:09Z","timestamp":1471023549000},"page":"e1005053","update-policy":"https:\/\/doi.org\/10.1371\/journal.pcbi.corrections_policy","source":"Crossref","is-referenced-by-count":30,"title":["Defining the Product Chemical Space of Monoterpenoid Synthases"],"prefix":"10.1371","volume":"12","author":[{"given":"Boxue","family":"Tian","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"C. Dale","family":"Poulter","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matthew P.","family":"Jacobson","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"340","published-online":{"date-parts":[[2016,8,12]]},"reference":[{"key":"ref1","doi-asserted-by":"crossref","first-page":"1621","DOI":"10.1016\/j.phytochem.2009.07.030","article-title":"Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants","volume":"70","author":"J Degenhardt","year":"2009","journal-title":"Phytochemistry"},{"key":"ref2","doi-asserted-by":"crossref","first-page":"1788","DOI":"10.1126\/science.277.5333.1788","article-title":"Biochemistry\u2014Creating isoprenoid diversity","volume":"277","author":"JC Sacchettini","year":"1997","journal-title":"Science"},{"key":"ref3","doi-asserted-by":"crossref","first-page":"470","DOI":"10.1038\/180470a0","article-title":"The Chemistry of Terpenoid Compounds","volume":"180","author":"AJ Birch","year":"1957","journal-title":"Nature"},{"key":"ref4","doi-asserted-by":"crossref","first-page":"1124","DOI":"10.1002\/anie.201103110","article-title":"Terpene biosynthesis: modularity rules","volume":"51","author":"E Oldfield","year":"2012","journal-title":"Angew Chem Int Ed Engl"},{"key":"ref5","doi-asserted-by":"crossref","first-page":"3412","DOI":"10.1021\/cr050286w","article-title":"Structural biology and chemistry of the terpenoid cyclases","volume":"106","author":"DW Christianson","year":"2006","journal-title":"Chem Rev"},{"key":"ref6","doi-asserted-by":"crossref","first-page":"1035","DOI":"10.1039\/c1np00006c","article-title":"Biosynthesis via carbocations: theoretical studies on terpene formation","volume":"28","author":"DJ Tantillo","year":"2011","journal-title":"Nat Prod Rep"},{"key":"ref7","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1006\/abbi.2001.2442","article-title":"Mechanism of monoterpene cyclization: stereochemical aspects of the transformation of noncyclizable substrate analogs by recombinant (-)-limonene synthase, (+)-bornyl diphosphate synthase, and (-)-pinene synthase","volume":"392","author":"W Schwab","year":"2001","journal-title":"Arch Biochem Biophys"},{"key":"ref8","doi-asserted-by":"crossref","first-page":"12632","DOI":"10.1021\/ja203342p","article-title":"Physical constraints on sesquiterpene diversity arising from cyclization of the eudesm-5-yl carbocation","volume":"133","author":"BA Hess Jr.","year":"2011","journal-title":"J Am Chem Soc"},{"key":"ref9","doi-asserted-by":"crossref","first-page":"7999","DOI":"10.1021\/ja9005332","article-title":"Consequences of conformational preorganization in sesquiterpene biosynthesis: theoretical studies on the formation of the bisabolene, curcumene, acoradiene, zizaene, cedrene, duprezianene, and sesquithuriferol sesquiterpenes","volume":"131","author":"YJ Hong","year":"2009","journal-title":"J Am Chem Soc"},{"key":"ref10","doi-asserted-by":"crossref","first-page":"D521","DOI":"10.1093\/nar\/gkt1130","article-title":"The Structure-Function Linkage Database","volume":"42","author":"E Akiva","year":"2014","journal-title":"Nucleic Acids Res"},{"key":"ref11","doi-asserted-by":"crossref","first-page":"9950","DOI":"10.1021\/bi201312u","article-title":"The Enzyme Function Initiative","volume":"50","author":"JA Gerlt","year":"2011","journal-title":"Biochemistry"},{"key":"ref12","doi-asserted-by":"crossref","first-page":"1078","DOI":"10.1038\/nature04607","article-title":"Designed divergent evolution of enzyme function","volume":"440","author":"Y Yoshikuni","year":"2006","journal-title":"Nature"},{"key":"ref13","doi-asserted-by":"crossref","first-page":"e1003874","DOI":"10.1371\/journal.pcbi.1003874","article-title":"Predicting the functions and specificity of triterpenoid synthases: a mechanism-based multi-intermediate docking approach","volume":"10","author":"BX Tian","year":"2014","journal-title":"PLoS Comput Biol"},{"key":"ref14","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1016\/j.tibs.2014.05.006","article-title":"Leveraging structure for enzyme function prediction: methods, opportunities, and challenges","volume":"39","author":"MP Jacobson","year":"2014","journal-title":"Trends Biochem Sci"},{"key":"ref15","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/S1574-1400(08)00012-1","article-title":"PubChem: Integrated Platform of Small Molecules and Biological Activities","volume":"Vol 4","author":"EE Bolton","year":"2008","journal-title":"Annual Reports in Computational Chemistry"},{"key":"ref16","doi-asserted-by":"crossref","first-page":"742","DOI":"10.1021\/ci100050t","article-title":"Extended-connectivity fingerprints","volume":"50","author":"D Rogers","year":"2010","journal-title":"J Chem Inf Model"},{"key":"ref17","doi-asserted-by":"crossref","first-page":"13857","DOI":"10.1021\/jp3091396","article-title":"Catalytic mechanism and product specificity of oxidosqualene-lanosterol cyclase: a QM\/MM study","volume":"116","author":"BX Tian","year":"2012","journal-title":"J Phys Chem B"},{"key":"ref18","doi-asserted-by":"crossref","first-page":"6349","DOI":"10.1021\/ja910134x","article-title":"Challenges posed to bornyl diphosphate synthase: diverging reaction mechanisms in monoterpenes","volume":"132","author":"M Weitman","year":"2010","journal-title":"J Am Chem Soc"},{"key":"ref19","doi-asserted-by":"crossref","first-page":"5370","DOI":"10.1002\/ejoc.201500518","article-title":"Isomerization of the 2-Norbornyl Carbocation","author":"KA Lobb","year":"2015","journal-title":"European Journal of Organic Chemistry"},{"key":"ref20","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1039\/c3sc53293c","article-title":"Predicting pathways for terpene formation from first principles\u2014routes to known and new sesquiterpenes","volume":"5","author":"M Isegawa","year":"2014","journal-title":"Chem Sci"},{"key":"ref21","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1021\/ci00023a024","article-title":"Investigation of Carbocationic Rearrangements by the Icar Program","volume":"35","author":"VV Shcherbukhin","year":"1995","journal-title":"Journal of Chemical Information and Computer Sciences"},{"key":"ref22","doi-asserted-by":"crossref","first-page":"2864","DOI":"10.1021\/ci300415d","article-title":"Enumeration of 166 billion organic small molecules in the chemical universe database GDB-17","volume":"52","author":"L Ruddigkeit","year":"2012","journal-title":"J Chem Inf Model"},{"key":"ref23","doi-asserted-by":"crossref","first-page":"5661","DOI":"10.1073\/pnas.1505127112","article-title":"Computational-guided discovery and characterization of a sesquiterpene synthase from Streptomyces clavuligerus","volume":"112","author":"JY Chow","year":"2015","journal-title":"Proc Natl Acad Sci U S A"},{"key":"ref24","unstructured":"Suite Schr\u00f6dinger 2014 Impact version 6.5; Prime version 3.8; MacroModel, version 10.5."},{"key":"ref25","doi-asserted-by":"crossref","first-page":"1101","DOI":"10.1002\/jcc.20425","article-title":"RM1: a reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I","volume":"27","author":"GB Rocha","year":"2006","journal-title":"J Comput Chem"},{"key":"ref26","doi-asserted-by":"crossref","first-page":"1815","DOI":"10.1126\/science.277.5333.1815","article-title":"Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase","volume":"277","author":"CM Starks","year":"1997","journal-title":"Science"},{"key":"ref27","doi-asserted-by":"crossref","first-page":"7652","DOI":"10.1002\/anie.201403648","article-title":"Induced-fit mechanism in class I terpene cyclases","volume":"53","author":"P Baer","year":"2014","journal-title":"Angew Chem Int Ed Engl"}],"container-title":["PLOS Computational Biology"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/dx.plos.org\/10.1371\/journal.pcbi.1005053","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,7,5]],"date-time":"2022-07-05T22:13:50Z","timestamp":1657059230000},"score":1,"resource":{"primary":{"URL":"https:\/\/dx.plos.org\/10.1371\/journal.pcbi.1005053"}},"subtitle":[],"editor":[{"given":"Jacquelyn S.","family":"Fetrow","sequence":"first","affiliation":[],"role":[{"role":"editor","vocabulary":"crossref"}]}],"short-title":[],"issued":{"date-parts":[[2016,8,12]]},"references-count":27,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2016,8,12]]}},"URL":"https:\/\/doi.org\/10.1371\/journal.pcbi.1005053","relation":{},"ISSN":["1553-7358"],"issn-type":[{"value":"1553-7358","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,8,12]]}}}