{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T03:27:30Z","timestamp":1792121250748,"version":"4.4.0"},"reference-count":110,"publisher":"Oxford University Press (OUP)","issue":"2","license":[{"start":{"date-parts":[[2024,8,22]],"date-time":"2024-08-22T00:00:00Z","timestamp":1724284800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22H02203"],"award-info":[{"award-number":["JP22H02203"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22H02203"],"award-info":[{"award-number":["JP22H02203"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2025,2,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Oxygenic phototrophs use chlorophylls (Chls) as photosynthetically active pigments. A variety of Chl molecules have been found in photosynthetic organisms, including green plants, algae and cyanobacteria. Here, we review their molecular structures with stereochemistry, occurrence in light-harvesting antennas and reaction centers, biosyntheses in the late stage, chemical stabilities and visible absorption maxima in diethyl ether. The observed maxima are comparable to those of semisynthetic Chl analogs, methyl pyropheophorbides, in dichloromethane. The effects of their peripheral substituents and core \u03c0-conjugation on the maxima of the monomeric states are discussed. Notably, the oxidation along the molecular x-axis in Chl-a produces its accessory pigments, Chls-b\/c, and introduction of an electron-withdrawing formyl group along the y-axis perpendicular to the x-axis affords far-red light absorbing Chls-d\/f.<\/jats:p>","DOI":"10.1093\/pcp\/pcae094","type":"journal-article","created":{"date-parts":[[2024,8,18]],"date-time":"2024-08-18T02:17:03Z","timestamp":1723947423000},"page":"153-167","source":"Crossref","is-referenced-by-count":49,"title":["Chlorophyll Pigments and Their Synthetic Analogs"],"prefix":"10.1093","volume":"66","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4797-0349","authenticated-orcid":false,"given":"Hitoshi","family":"Tamiaki","sequence":"first","affiliation":[{"name":"Graduate School of Life Sciences, Ritsumeikan University , Kusatsu, Shiga, 525-8577","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saki","family":"Kichishima","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences, Ritsumeikan University , Kusatsu, Shiga, 525-8577","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2024,8,22]]},"reference":[{"key":"2025030421594972700_R1","doi-asserted-by":"crossref","first-page":"205","DOI":"10.2116\/analsci.17.205","article-title":"Detection of chlorophyll d\u2032 and pheophytin a in a chlorophyll d-dominating oxygenic photosynthetic prokaryote Acaryochloris marina","volume":"17","author":"Akiyama","year":"2001","journal-title":"Anal. 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Phycol."},{"key":"2025030421594972700_R18","doi-asserted-by":"crossref","DOI":"10.1016\/j.bbabio.2024.149032","article-title":"Recent structural discoveries of photosystems I and II acclimated to absorb far-red light","volume":"1865","author":"Gisriel","year":"2024","journal-title":"Biochim. Biophys. Acta Bioenerg."},{"key":"2025030421594972700_R19","article-title":"Structure of a monomeric photosystem II core complex from a cyanobacterium acclimated to far-red light reveals the functions of chlorophylls d and f","volume":"298","author":"Gisriel","year":"2022","journal-title":"J. Biol. Chem."},{"key":"2025030421594972700_R20","doi-asserted-by":"crossref","first-page":"40015","DOI":"10.1021\/acsomega.3c05896","article-title":"Excitation energy transfer between higher excited states of photosynthetic pigments: 2. 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Commun."},{"key":"2025030421594972700_R23","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/S0005-2728(03)00081-1","article-title":"Chlorophylls of the c family: absolute configuration and inhibition of NADPH:protochlorophyllide oxidoreductase","volume":"1605","author":"Helfrich","year":"2003","journal-title":"Biochim. Biophys. Acta Bioenerg."},{"key":"2025030421594972700_R24","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3354\/meps08588","article-title":"Modelling the effects of chromatic adaptation on phytoplankton community structure in the oligotrophic ocean","volume":"406","author":"Hickman","year":"2010","journal-title":"Mar. Ecol. Prog. Ser."},{"key":"2025030421594972700_R25","doi-asserted-by":"crossref","first-page":"1701","DOI":"10.1039\/b9pp00018f","article-title":"Demetalation kinetics of natural chlorophylls purified from oxygenic photosynthetic organisms: effect of the formyl groups conjugated directly to the chlorin \u03c0-macrocycle","volume":"8","author":"Hirai","year":"2009","journal-title":"Photochem. Photobiol. Sci."},{"key":"2025030421594972700_R26","doi-asserted-by":"crossref","DOI":"10.1126\/science.aaf9178","article-title":"Light-dependent chlorophyll f synthase is a highly divergent paralog of PsbA of photosystem II","volume":"353","author":"Ho","year":"2016","journal-title":"Science"},{"key":"2025030421594972700_R27","doi-asserted-by":"crossref","first-page":"1788","DOI":"10.1126\/science.272.5269.1788","article-title":"Structural basis of light harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae","volume":"272","author":"Hofmann","year":"1996","journal-title":"Science"},{"key":"2025030421594972700_R28","doi-asserted-by":"crossref","first-page":"637","DOI":"10.3891\/acta.chem.scand.33b-0637","article-title":"Chlorophylls. VI. Epimerization and enolization of chlorophyll a and its magnesium-free derivatives","volume":"33","author":"Hynninen","year":"1979","journal-title":"Acta Chem. Scand. Ser. B"},{"key":"2025030421594972700_R29","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1246\/cl.1982.1003","article-title":"Revised method for calculation of group electronegativities","volume":"11","author":"Inamoto","year":"1982","journal-title":"Chem. Lett."},{"key":"2025030421594972700_R30","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1126\/science.adg7921","article-title":"A chlorophyll c synthase widely co-opted by phytoplankton","volume":"382","author":"Jiang","year":"2023","journal-title":"Science"},{"key":"2025030421594972700_R31","doi-asserted-by":"crossref","first-page":"594","DOI":"10.1016\/j.cub.2023.12.068","article-title":"Biosynthesis of chlorophyll c in a dinoflagellate and heterologous production in planta","volume":"34","author":"Jinkerson","year":"2024","journal-title":"Curr. Biol."},{"key":"2025030421594972700_R32","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1038\/35082000","article-title":"Three-dimensional structure of cyanobacterial photosystem I at 2.5\u2009\u00c5 resolution","volume":"411","author":"Jordan","year":"2001","journal-title":"Nature"},{"key":"2025030421594972700_R33","doi-asserted-by":"crossref","first-page":"1132","DOI":"10.1021\/ja01272a037","article-title":"The rate of conversion of chlorophyll to pheophytin","volume":"60","author":"Joslyn","year":"1938","journal-title":"J. Am. Chem. Soc."},{"key":"2025030421594972700_R34","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1007\/s11120-021-00827-1","article-title":"Accumulation of geranylgeranylated chlorophylls in the pigment-protein complexes of Arabidopsis thaliana acclimated to green light: effects on the organization of light-harvesting complex II and photosystem II functions","volume":"149","author":"Karlick\u00fd","year":"2021","journal-title":"Photosynth. Res."},{"key":"2025030421594972700_R35","doi-asserted-by":"crossref","DOI":"10.1073\/pnas.2319658121","article-title":"The structure of PSI-LHCI from Cyanidium caldarium provides evolutionary insights into conservation and diversity of red-lineage LHCs","volume":"121","author":"Kato","year":"2024","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"2025030421594972700_R36","doi-asserted-by":"crossref","DOI":"10.1038\/s41467-019-13898-5","article-title":"Structural basis for the adaptation and function of chlorophyll f in photosystem I","volume":"11","author":"Kato","year":"2020","journal-title":"Nat. Commun."},{"key":"2025030421594972700_R37","doi-asserted-by":"crossref","DOI":"10.1016\/j.tet.2020.130948","article-title":"Synthesis of tin(IV) complexes of chlorophyll-a derivatives with two halides as axial ligands and their optical properties in solution","volume":"76","author":"Kawamoto","year":"2020","journal-title":"Tetrahedron"},{"key":"2025030421594972700_R38","doi-asserted-by":"crossref","first-page":"3246","DOI":"10.1016\/j.jmb.2019.05.046","article-title":"Crystal structure of dihydro-heme d1 dehydrogenase NirN from Pseudomonas aeruginosa reveals amino acid residues essential for catalysis","volume":"431","author":"Kl\u00fcnemann","year":"2019","journal-title":"J. Mol. Biol."},{"key":"2025030421594972700_R39","first-page":"47","volume-title":"Photosynthesis","author":"Kobayashi","year":"2013"},{"key":"2025030421594972700_R40","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/0005-2728(88)90254-X","article-title":"Chlorophyll a\u2032\/P-700 and pheophytin a\/P-680 stoichiometries in higher plants and cyanobacteria determined by HPLC analysis","volume":"936","author":"Kobayashi","year":"1988","journal-title":"Biochim. Biophys. Acta Bioenerg."},{"key":"2025030421594972700_R41","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1007\/s11120-016-0283-5","article-title":"Unique chlorophylls in picoplankton Prochlorococcus sp. \u201cPhysicochemical properties of divinyl chlorophylls, and the discovery of monovinyl chlorophyll b as well as divinyl chlorophyll b in the species Prochlorococcus NIES-2086\u201d","volume":"130","author":"Komatsu","year":"2016","journal-title":"Photosynth. Res."},{"key":"2025030421594972700_R42","doi-asserted-by":"crossref","DOI":"10.2142\/biophysico.bppb-v19.0013","article-title":"Recent advances in single-molecule spectroscopy studies on light-harvesting processes in oxygenic photosynthesis","volume":"19","author":"Kondo","year":"2022","journal-title":"Biophys. Physicobiol."},{"key":"2025030421594972700_R43","doi-asserted-by":"crossref","DOI":"10.7554\/eLife.50871","article-title":"Substantial near-infrared radiation-driven photosynthesis of chlorophyll f-containing cyanobacteria in a natural habitat","volume":"9","author":"K\u00fchl","year":"2020","journal-title":"eLife"},{"key":"2025030421594972700_R44","doi-asserted-by":"crossref","first-page":"11349","DOI":"10.1016\/j.tet.2004.09.091","article-title":"Syntheses and optical properties of stable\u00a08-alkylidene-bacteriochlorins mimicking the molecular structures of natural bacteriochlorophylls-b and g","volume":"60","author":"Kunieda","year":"2004","journal-title":"Tetrahedron"},{"key":"2025030421594972700_R45","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1071\/FP14350","article-title":"Novel chlorophylls and new directions in photosynthesis research","volume":"42","author":"Li","year":"2015","journal-title":"Funct. Plant Biol."},{"key":"2025030421594972700_R46","doi-asserted-by":"crossref","first-page":"1292","DOI":"10.1016\/j.bbabio.2012.02.026","article-title":"Extinction coefficient for red-shifted chlorophylls: chlorophyll d and chlorophyll f","volume":"1817","author":"Li","year":"2012","journal-title":"Biochim. Biophys. Acta Bioenerg."},{"key":"2025030421594972700_R47","volume-title":"Chlorophylls","author":"Linnanto","year":"2022"},{"key":"2025030421594972700_R48","doi-asserted-by":"crossref","first-page":"14311","DOI":"10.1021\/ja8050298","article-title":"Highly selective synthesis of the ring-B reduced chlorins by ferric chloride-mediated oxidation of bacteriochlorins: effects of the fused imide vs isocyclic ring on photophysical and electrochemical properties","volume":"130","author":"Liu","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"2025030421594972700_R49","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1007\/s11120-013-9829-y","article-title":"Chlorophyll d and Acaryochloris marina: current status","volume":"116","author":"Loughlin","year":"2013","journal-title":"Photosynth. Res."},{"key":"2025030421594972700_R50","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1016\/0040-4020(95)00944-2","article-title":"Nucleophilic reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene and 1,5-diazabicyclo[4.3.0]non-5-ene with methyl pheophorbide a. Unexpected products","volume":"52","author":"Ma","year":"1996","journal-title":"Tetrahedron"},{"key":"2025030421594972700_R51","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0021-9258(18)72109-1","article-title":"Chlorophyll d, a green pigment of red algae","volume":"151","author":"Manning","year":"1943","journal-title":"J. Biol. Chem."},{"key":"2025030421594972700_R52","doi-asserted-by":"crossref","first-page":"3080","DOI":"10.1246\/bcsj.65.3080","article-title":"Epimerization of chlorophyll derivatives. V. Effects of the central magnesium and ring substituents on the epimerization of chlorophyll derivatives","volume":"65","author":"Mazaki","year":"1992","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2025030421594972700_R53","doi-asserted-by":"crossref","DOI":"10.1038\/383402a0","article-title":"Chlorophyll d as a major pigment","volume":"383","author":"Miyashita","year":"1996","journal-title":"Nature"},{"key":"2025030421594972700_R54","doi-asserted-by":"crossref","first-page":"3682","DOI":"10.1021\/acs.biochem.7b00381","article-title":"Molecular structures and functions of chlorophylls-a esterified with geranylgeranyl, dihydrogeranylgeranyl and tetrahydrogeranylgeranyl groups at the 17-propionate residue in a diatom, Chaetoceros calcitrans","volume":"56","author":"Mizoguchi","year":"2017","journal-title":"Biochemistry"},{"key":"2025030421594972700_R55","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1111\/j.1751-1097.2009.00667.x","article-title":"Exclusive observation of the (132R)-enantiomer of chlorophyll-c from a diatom Chaetoceros calcitrans","volume":"86","author":"Mizoguchi","year":"2010","journal-title":"Photochem. Photobiol."},{"key":"2025030421594972700_R56","doi-asserted-by":"crossref","first-page":"1467","DOI":"10.1016\/j.bbabio.2011.07.008","article-title":"The stereochemistry of chlorophyll-c3 from the haptophyte Emiliania huxleyi: the (132R)-enantiomers of chlorophylls-c are exclusively selected as the photosynthetically active pigments in chromophyte algae","volume":"1807","author":"Mizoguchi","year":"2011","journal-title":"Biochim. Biophys. Acta Bioenerg."},{"key":"2025030421594972700_R57","doi-asserted-by":"crossref","first-page":"2120","DOI":"10.1039\/b900802k","article-title":"Stereochemical determination of the unique acrylate moiety at the 17-position in chlorophylls-c from a diatom Chaetoceros calcitrans and its effect upon electronic absorption properties","volume":"7","author":"Mizoguchi","year":"2009","journal-title":"Org. Biomol. Chem."},{"key":"2025030421594972700_R58","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1038\/nature08950","article-title":"X-ray crystal structure of the light-independent protochlorophyllide reductase","volume":"465","author":"Muraki","year":"2010","journal-title":"Nature"},{"key":"2025030421594972700_R59","doi-asserted-by":"crossref","DOI":"10.1038\/s41467-022-29294-5","article-title":"Structural basis for different types of hetero-tetrameric light-harvesting complexes in a diatom PSII-FCPII supercomplex","volume":"13","author":"Nagao","year":"2022","journal-title":"Nat. Commun."},{"key":"2025030421594972700_R60","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1105\/tpc.104.027276","article-title":"Identification of a vinyl reductase gene for chlorophyll synthesis in Arabidopsis thaliana and implications for the evolution of Prochlorococcus species","volume":"17","author":"Nagata","year":"2005","journal-title":"Plant Cell"},{"key":"2025030421594972700_R61","doi-asserted-by":"crossref","first-page":"509","DOI":"10.2116\/analsci.17.509","article-title":"Normal-phase HPLC separation of possible biosynthetic intermediates of pheophytin a and chlorophyll a\u2032","volume":"17","author":"Nakamura","year":"2001","journal-title":"Anal. Sci."},{"key":"2025030421594972700_R62","doi-asserted-by":"crossref","DOI":"10.1016\/j.jphotochem.2023.115118","article-title":"Synthesis of C3-fluoroalkylated chlorophyll-a derivatives and fine tuning of their optical properties by the fluorination degree","volume":"446","author":"Nishibori","year":"2024","journal-title":"J. Photochem. Photobiol. A: Chem."},{"key":"2025030421594972700_R63","doi-asserted-by":"crossref","first-page":"1905","DOI":"10.1246\/bcsj.70.1905","article-title":"Convenient preparation of pheophytin b from plant extract through the C7-reduced intermediate","volume":"70","author":"Oba","year":"1997","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2025030421594972700_R64","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1023\/A:1020816128794","article-title":"Which side of \u03c0-macrocycle plane of (bacterio)chlorophylls is favored for binding of the fifth ligand?","volume":"74","author":"Oba","year":"2002","journal-title":"Photosynth. Res."},{"key":"2025030421594972700_R65","doi-asserted-by":"crossref","first-page":"5733","DOI":"10.1016\/j.bmc.2005.06.016","article-title":"Effects of peripheral substituents on diastereoselectivity of the fifth ligand-binding to chlorophylls, and nomenclature of the asymmetric axial coordination sites","volume":"13","author":"Oba","year":"2005","journal-title":"Bioorg. Med. Chem."},{"key":"2025030421594972700_R66","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1142\/S1088424614500710","article-title":"Asymmetry of chlorophylls in photosynthetic proteins: from the viewpoint of coordination chemistry","volume":"18","author":"Oba","year":"2014","journal-title":"J. Porphyr. 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