{"refrec":{"BRefID":340125,"RR":"<b>Holzheimer, M.; Sinninghe Damste, J.S.; Schouten, S.; Havenith, R.W.A.; Minnaard, A.J.</b> (2021). Total synthesis of the alleged structure of crenarchaeol enables structure revision. <i>Angew. Chem. 133(32)</i>: 17645-17654. <a href=\"https://doi.org/10.1002/ange.202105384\" target=\"_blank\">https://doi.org/10.1002/ange.202105384</a>","BEntID":336760,"PublicFlag":1,"CheckedFlag":0,"wosflag":1,"vabbflag":0,"RefStringPartII":". <i>Angew. Chem. 133(32)</i>: 17645-17654. <a href=\"https://doi.org/10.1002/ange.202105384\" target=\"_blank\">https://doi.org/10.1002/ange.202105384</a>","DocTypID":8,"DocType":"Journal article","MarineFlag":0,"FreshFlag":0,"BrackishFlag":0,"TerrestrialFlag":0,"Authorstring":"Holzheimer, M.; Sinninghe Damste, J.S.; Schouten, S.; Havenith, R.W.A.; Minnaard, A.J.","OrigTitleTranslFlag":0,"Authorstringtrunc":"Holzheimer, M. <i>et al.</i>","Englishabstract":"Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.","AbstractOtherLang":null,"BibLvlCode":"AS","StandardTitle":"Total synthesis of the alleged structure of crenarchaeol enables structure revision","OrigTitleLangCode":"en","OrigTitleLangCodeExtended":"eng","OrigTitleLangID":15,"DateLastModified":{"date":"2026-06-10 01:32:37.853785","timezone_type":1,"timezone":"+02:00"},"UserAccessRight":null,"UserAccID":null,"AuthorKeywords":null,"OtherDescriptors":null,"Notes":null,"AnaPub":2021,"MonPub":null,"DateUpdate":"2021-08-31","DateCreate":"2021-07-14","SecASFANote":null,"ConfID":null,"PeerRev":1,"VlizCoreFlag":1,"WoScode":"WOS:000668279600001","VABBcode":null,"OpenAcc":1,"DOI":"10.1002/ange.202105384"},"refs":null,"anarec":{"AnaID":340125,"PubliDate":2021,"Pagination":"17645-17654","XtraPublOfAnaID":null,"ISBN":null,"Volume":"133","Issue":"32","BRefMon":null,"BRefMonRR":null,"BRefXtra":null,"BRefXtraRR":null,"SerBRefID":42104,"SerRR":"Angewandte Chemie. Wiley: Weinheim.  ISSN 1433-7851; e-ISSN 1521-3773","StandardTitleSer":"Angewandte Chemie","ISSN":"1433-7851","AbbrevSer":"Angew. Chem.","StandardTitleMon":null,"StartPage":17645,"Pages":10,"ToPubliDate":null,"BRefBibLvlCode":"S","SerNotes":null},"monrec":null,"serrec":null,"relations":null,"relationsRev":null,"addrec":null,"othpubs":null,"ownerships":null,"authors":[{"AutName":"Holzheimer","Firstname":"Mira","Initials":"M.","Affiliation":null,"Discriminator":null,"CorporateFlag":0,"BEntID":336760,"AutID":440029,"OrderNr":1,"DegrID":null,"EditorFlag":0,"CorrespFlag":0,"IllustratorFlag":0,"ReviserFlag":0,"TranslatorFlag":0,"InsAcronym":null,"InsFSN":null,"ORCID":null,"PersID":null,"InsID":null},{"AutName":"Sinninghe Damste","Firstname":null,"Initials":"J.S.","Affiliation":null,"Discriminator":null,"CorporateFlag":0,"BEntID":336760,"AutID":206415,"OrderNr":2,"DegrID":null,"EditorFlag":0,"CorrespFlag":0,"IllustratorFlag":0,"ReviserFlag":0,"TranslatorFlag":0,"InsAcronym":"MMB","InsFSN":"Koninklijk Nederlands Instituut voor Onderzoek der Zee; Marine Microbiology and Biogeochemistry","ORCID":"0000-0002-8683-1854","PersID":29942,"InsID":13655},{"AutName":"Schouten","Firstname":null,"Initials":"S.","Affiliation":null,"Discriminator":null,"CorporateFlag":0,"BEntID":336760,"AutID":233117,"OrderNr":3,"DegrID":null,"EditorFlag":0,"CorrespFlag":0,"IllustratorFlag":0,"ReviserFlag":0,"TranslatorFlag":0,"InsAcronym":"MMB","InsFSN":"Koninklijk Nederlands Instituut voor Onderzoek der Zee; Marine Microbiology and Biogeochemistry","ORCID":null,"PersID":15342,"InsID":13655},{"AutName":"Havenith","Firstname":"Remco","Initials":"R.W.A.","Affiliation":null,"Discriminator":null,"CorporateFlag":0,"BEntID":336760,"AutID":461259,"OrderNr":4,"DegrID":null,"EditorFlag":0,"CorrespFlag":0,"IllustratorFlag":0,"ReviserFlag":0,"TranslatorFlag":0,"InsAcronym":null,"InsFSN":null,"ORCID":null,"PersID":null,"InsID":null},{"AutName":"Minnaard","Firstname":"Adriaan","Initials":"A.J.","Affiliation":"Stratingh Institute for Chemistry, University of Groningen","Discriminator":null,"CorporateFlag":0,"BEntID":336760,"AutID":183821,"OrderNr":5,"DegrID":null,"EditorFlag":0,"CorrespFlag":0,"IllustratorFlag":0,"ReviserFlag":0,"TranslatorFlag":0,"InsAcronym":null,"InsFSN":null,"ORCID":null,"PersID":null,"InsID":null}],"mapdetails":null,"datasets":null,"monographs":null,"monparts":null,"serparts":null,"BEntOpen":336760,"BEntPrivate":null,"availability":[{"BInstID":363593,"LibID":36,"BRefID":340125,"EmbargoDate":null,"FullEmbargoDate":null,"PhysMedID":16,"hasOCRd":1,"ShelfLocCode":"363593","RFID":null,"PaidValue":null,"Medium":"Server","Description":"VLIZ Open Access","Acronym":"VLIZ","Library":"Vlaams Instituut voor de Zee","DutchTerm":"Open access","URL":null,"ClassifID":53,"Classification":"Open access","ReqLink":null,"ClassifTypID":1,"URLLocation":"https://www.vliz.be/imisdocs/publications/","SubDir":null,"InternalReq":0,"LoggedInReq":0,"Disclaimer":null,"DutchDisclaimer":null,"FileFormat":".pdf","FileDescr":"pdf","InsPub":1,"InsID":36,"FileFormID":6,"LendableFlag":1,"PublicFlag":1,"orderLib":"A","Notes":null,"AccConID":null,"AccessConstraint":null,"LicURL":null},{"BInstID":367616,"LibID":2779,"BRefID":340125,"EmbargoDate":null,"FullEmbargoDate":null,"PhysMedID":16,"hasOCRd":1,"ShelfLocCode":"367616","RFID":null,"PaidValue":null,"Medium":"Server","Description":null,"Acronym":null,"Library":"NIOZ","DutchTerm":null,"URL":null,"ClassifID":260,"Classification":"NIOZ Open Repository","ReqLink":null,"ClassifTypID":1,"URLLocation":"https://www.vliz.be/imisdocs/publications/","SubDir":1,"InternalReq":null,"LoggedInReq":null,"Disclaimer":"Disclaimer_NIOZ","DutchDisclaimer":null,"FileFormat":".pdf","FileDescr":"pdf","InsPub":1,"InsID":397,"FileFormID":6,"LendableFlag":null,"PublicFlag":1,"orderLib":"NIOZ","Notes":null,"AccConID":null,"AccessConstraint":null,"LicURL":null}],"litstyles":null,"thespers":null,"arch2discl":805,"SERpubls":[{"PublName":"Wiley","City":"Weinheim"}],"MONpubls":null,"pictures":[],"thestermsPath":null,"thestermsASFA":null,"taxtermsASFA":null,"geotermsASFA":null,"collections":null,"conf":null,"proj":null,"Physdatasets":null,"spcols":{"805":{"SpName":"Koninklijk Nederlands Instituut voor Onderzoek der Zee","SpColID":805,"ParSpColID":null,"TopParID":null,"ShortName":"NIOZ","URLLocation":"https://www.vliz.be/imis/nioz/imis.php?refid=","LibID":2779,"OpenRepoFlag":1,"SpTypID":1,"TopParIDNotWebsite":null,"SpColPath":"NIOZ"}},"doi":null,"publs":null,"serparttypes":null,"monauthors":null,"MParts":null,"SParts":null,"hLibs":null,"langs":[{"BEntID":336760,"AbstractFlag":0,"LangID":15,"LangCode":"en","Lang":"English","DutchTerm":"Engels","LangCodeExtended":"eng"},{"BEntID":336760,"AbstractFlag":1,"LangID":15,"LangCode":"en","Lang":"English","DutchTerm":"Engels","LangCodeExtended":"eng"}],"urls":[{"URL":"https://doi.org/10.1002/ange.202105384","externalID":"10.1002/ange.202105384","URLTypeCode":"DOI","URLID":95383,"URLTypID":13,"URLType":"DOI","URLPrefix":"http://dx.doi.org/"}],"thesterms":null,"taxterms":null,"geoterms":null,"othterms":null,"asfacodes":null,"asfa2codes":null,"thestermsFRIS":null,"taxtermsFRIS":null,"geotermsFRIS":null,"othtermsFRIS":null,"resmessage":"","complete":1,"sessions":{"newSesName":"Leonne.van.der.Weegen@nioz.nl","newSesDate":{"date":"2021-07-14 09:58:12.097000","timezone_type":3,"timezone":"Europe/Brussels"},"updSesName":"Leonne.van.der.Weegen@nioz.nl","updSesDate":{"date":"2021-08-31 10:40:35.057000","timezone_type":3,"timezone":"Europe/Brussels"}}}
