Stereochemical assignment of the unique electron acceptor 5′-hydroxyphylloquinone, a polar analog of vitamin K₁ in photosystem I

References

• Jordan P, Fromme P, Witt H, et al. Three-dimensional structure of cyanobacterial photosystem I at 2.5 Å resolution. Nature. 2001;411:909–917.10.1038/35082000
   PubMed Web of Science ®Google Scholar
• Henninger MD, Bhagavan HN, Crane FL. Comparative studies on plastoquinones: I. Evidence for three quinones in the blue-green alga, Anacystis nidulans. Arch Biochem Biophys. 1965;110:69–74.10.1016/0003-9861(65)90155-4
   PubMed Web of Science ®Google Scholar
• Henninger MD. Hydrogenase in chlorella: qualitative differences in quinone composition. Biochem Biophys Res Commun. 1965;19:233–236.10.1016/0006-291X(65)90510-3
   PubMed Web of Science ®Google Scholar
• Allen CF, Franke H, Hirayama O. Identification of a plastoquinone and two naphthoquinones in Anacystis nidulans by NMR and mass spectroscopy. Biochem Biophys Res Commun. 1967;26:562–568.10.1016/0006-291X(67)90102-7
   PubMed Web of Science ®Google Scholar
• Law A, Thomas G, Threlfall DR. 5′-Monohydroxyphylloquinone from Anacystis and Euglena. Phytochemistry. 1973;12:1999–2004.10.1016/S0031-9422(00)91523-1
   Web of Science ®Google Scholar
• Ozawa S, Kosugi M, Kashino Y, et al. 5′-monohydroxyphylloquinone is the dominant naphthoquinone of PSI in the green alga Chlamydomonas reinhardtii. Plant cell Physiol. 2012;53:237–243.10.1093/pcp/pcr168
   PubMed Web of Science ®Google Scholar
• Knierzinger A, Walther W, Weber B, et al. Eine neue Methode zur stereochemischen Analyse offenkettiger terpenoider Carbonyl-Verbindungen. Helv Chim Acta. 1990;73:1087–1107.10.1002/hlca.v73:4
   Google Scholar
• Cane DE, Iyengar R, Shiao MS. Cyclonerodiol biosynthesis and the enzymic conversion of farnesyl to nerolidyl pyrophosphate. J Am Chem Soc. 1981;103:914–931.10.1021/ja00394a032
   Web of Science ®Google Scholar
• Lei B, Fallis AG. Regioselective control of allyl anions with cadmium chloride: α vs. γ condensation with aldehydes. Tetrahedron Lett. 1986;27:5193–5196.
   Web of Science ®Google Scholar
• Lei B, Fallis AG. Cadmium chloride mediated regiocontrol of dienolates and ketene thioacetals: γ condensation with aldehydes. Can J Chem. 1991;69:1450–1456.10.1139/v91-214
   Web of Science ®Google Scholar
• Suhara Y, Wada A, Tachibana Y, et al. Structure-activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines. Bioorg Med Chem. 2010;18:3116–3124.10.1016/j.bmc.2010.03.035
   PubMed Web of Science ®Google Scholar
• Hirschmann R, Miller R, Wendler NL. The synthesis of vitamin K1. J Am Chem Soc. 1954;76:4592–4594.10.1021/ja01647a026
   Web of Science ®Google Scholar
• Isler O, Rüegg R, Chopard-dit-Jean LH, et al. Synthese und Isolierung von vitamin K2 und isoprenologen Verbindungen. Helv Chim Acta. 1958;41:786–807.10.1002/hlca.v41:3
   Web of Science ®Google Scholar
• Suhara Y, Hirota Y, Nakagawa K, et al. Design and synthesis of biologically active analogues of vitamin K2: evaluation of their biological activities with cultured human cell lines. Bioorg Med Chem. 2008;16:3108–3117.10.1016/j.bmc.2007.12.025
   PubMed Web of Science ®Google Scholar
• Burnett AR, Thomson RH. Naturally occurring quinones. Part XII. Extractives from Tabebuia chrysantha nichols and other bignoniaceae. J Chem Soc C. 1968;50:850–853.10.1039/j39680000850
   Google Scholar
• Mayer H, Schudel P, Rüegg R, et al. Uber die chemie des vitamins. Die total synthese von (2R,4′R,8R)- und (2S,4′R,8′R)-α-tocophenol. Helv Chim Acta. 1963;46:650–671.10.1002/hlca.19630460225
   Web of Science ®Google Scholar
• Termath AO, Velder J, Stemmler RT, et al. Total synthesis of (2 RS)-α-tocopherol through Ni-catalyzed 1,4-addition to a chromenone intermediate. Eur J Org Chem. 2014;2014:3337–3340.10.1002/ejoc.v2014.16
   Web of Science ®Google Scholar
• List B, Lerner RA, Barbas CF III. Proline-catalyzed direct asymmetric aldol reactions. J Am Chem Soc. 2000;122:2395–2396.10.1021/ja994280y
   Web of Science ®Google Scholar
• List B, Pojarliev P, Biller WT, et al. The proline-catalyzed direct asymmetric three-component mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. J Am Chem Soc. 2002;124:827–833.10.1021/ja0174231
   PubMed Web of Science ®Google Scholar
• Berger TA, Berger BK. Chromatographic resolution of 7 of 8 stereoisomers of vitamin K1 on an amylose stationary phase using supercritical fluid chromatography. Chromatographia. 2013;76:549–552.10.1007/s10337-013-2428-4
   Web of Science ®Google Scholar
• Suga T, Ohta S, Nakai A, et al. Glycinoprenols: novel polyprenols possessing a phytyl residue from the leaves of soybean. J Org Chem. 1989;54(14):3390–3393.10.1021/jo00275a026
   Web of Science ®Google Scholar