In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenatedporphyrins.[1] The parent chlorin is an unstable compound which undergoes air oxidation to porphine.[2] The name chlorin derives from chlorophyll. Chlorophylls are magnesium-containing chlorins and occur as photosynthetic pigments in chloroplasts. The term "chlorin" strictly speaking refers to only compounds with the same ring oxidation state as chlorophyll.
The most abundant chlorin is the photosynthetic pigment chlorophyll. Chlorophylls have a fifth, ketone-containing ring unlike the chlorins. Diverse chlorophylls exists, such as chlorophyll a, chlorophyll b, chlorophyll d, chlorophyll e, chlorophyll f, and chlorophyll g. Chlorophylls usually feature magnesium as a central metal atom, replacing the two NH centers in the parent.[4]
Structures comparing porphin, chlorin, bacteriochlorin, and isobacteriochlorin.
Microbes produce two reduced variants of chlorin, bacteriochlorins and isobacteriochlorins. Bacteriochlorins are found in some bacteriochlorophylls; the ring structure is produced by Chlorophyllide a reductase (COR) reducing a chlorin ring at the C7-8 double boud.[5] Isobacteriochlorins are found in nature mostly as sirohydrochlorin, a biosynthetic intermediate of vitamin B12, produced without going through a chlorin. In living organisms, both are ultimately derived from uroporphyrinogen III, a near-universal intermediate in tetrapyrrole biosynthesis.[6]
Synthetic chlorinsedit
Numerous synthetic chlorins with different functional groups and/or ring modifications have been examined.[7]
Contracted chlorins can be synthesised by reduction of B(III)subporphyrin or by oxidation of corresponding B(III)subbacteriochlorin.[8] The B(III)subchlorins were directly synthesized as meso-ester B(III)subchlorin from meso-diester tripyrromethane, these class of compound showed very good fluorescence quantum yield and singlet oxygen producing efficiency[9][10]
Juse´lius, Jonas; Sundholm, Dage (2000). "The aromatic pathways of porphins, chlorins and bacteriochlorins". Physical Chemistry Chemical Physics. 2 (10): 2145–2151. Bibcode:2000PCCP....2.2145J. doi:10.1039/b000260g.
Referencesedit
^Gerard P. Moss (1988). "Nomenclature of Tetrapyrroles. Recommendations 1986". European Journal of Biochemistry. 178 (2): 277–328. doi:10.1111/j.1432-1033.1988.tb14453.x. PMID 3208761.
^Battersby, Alan R. (2000). "Tetrapyrroles: The pigments of life". Natural Product Reports. 17 (6): 507–526. doi:10.1039/b002635m. PMID 11152419.
^Spikes, John D. (July 1990). "New trends in photobiology". Journal of Photochemistry and Photobiology B: Biology. 6 (3): 259–274. doi:10.1016/1011-1344(90)85096-F. PMID 2120404.
^Chew, Aline Gomez Maqueo; Bryant, Donald A. (2007). "Chlorophyll Biosynthesis in Bacteria: The Origins of Structural and Functional Diversity". Annual Review of Microbiology. 61: 113–129. doi:10.1146/annurev.micro.61.080706.093242. PMID 17506685.
^Battersby, Alan R. (2000). "Tetrapyrroles: The pigments of life: A Millennium review". Natural Product Reports. 17 (6): 507–526. doi:10.1039/B002635M. PMID 11152419.
^Taniguchi, Masahiko; Lindsey, Jonathan S. (2017). "Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins". Chemical Reviews. 117 (2): 344–535. doi:10.1021/acs.chemrev.5b00696. OSTI 1534468. PMID 27498781.
^Osuka, Atsuhiro; Kim, Dongho (2008). "Synthesis and Characterization of meso-Aryl-Substituted Subchlorins". Journal of the American Chemical Society. 130 (2): 438–439. doi:10.1021/ja078042b. PMID 18095693.
^Chandra, Brijesh; Soman, Rahul; Sathish Kumar, B.; Jose, K. V. Jovan; Panda, Pradeepta K. (3 Dec 2020). "Meso-Free Boron(III)subchlorin and Its μ-Oxo Dimer with Interacting Chromophores". Organic Letters. 22 (24): 9735–9739. doi:10.1021/acs.orglett.0c03813. PMID 33270460. S2CID 227282229.
^Soman, Rahul; Chandra, Brijesh; Bhat, Ishfaq A.; Kumar, B. Sathish; Hossain, Sk Saddam; Nandy, Sridatri; Jose, K. V. Jovan; Panda, Pradeepta K. (15 Jul 2021). "A2B- and A3-Type Boron(III)Subchlorins Derived from meso-Diethoxycarbonyltripyrrane: Synthesis and Photophysical Exploration". The Journal of Organic Chemistry. 86 (15): 10280–10287. doi:10.1021/acs.joc.1c01001. PMID 34264670. S2CID 235959639.
December 14, 2023
chlorin, confused, with, chlorine, organic, chemistry, chlorins, tetrapyrrole, pigments, that, partially, hydrogenated, porphyrins, parent, chlorin, unstable, compound, which, undergoes, oxidation, porphine, name, chlorin, derives, from, chlorophyll, chlorophy. Not to be confused with chlorine In organic chemistry chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins 1 The parent chlorin is an unstable compound which undergoes air oxidation to porphine 2 The name chlorin derives from chlorophyll Chlorophylls are magnesium containing chlorins and occur as photosynthetic pigments in chloroplasts The term chlorin strictly speaking refers to only compounds with the same ring oxidation state as chlorophyll Chlorin NamesOther names 2 3 DihydroporphineIdentifiersCAS Number 2683 84 3 Y3D model JSmol Interactive imageChEBI CHEBI 36303 NChemSpider 58616 YPubChem CID 65106CompTox Dashboard EPA DTXSID30893669InChI InChI 1S C20H16N4 c1 2 14 10 16 5 6 18 23 16 12 20 8 7 19 24 20 11 17 4 3 15 22 17 9 13 1 21 14 h1 6 9 12 22 23H 7 8H2 b13 9 14 10 15 9 16 10 17 11 18 12 19 11 20 12 YKey UGADAJMDJZPKQX CEVVSZFKSA N YInChI 1 C20H16N4 c1 2 14 10 16 5 6 18 23 16 12 20 8 7 19 24 20 11 17 4 3 15 22 17 9 13 1 21 14 h1 6 9 12 22 23H 7 8H2 b13 9 14 10 15 9 16 10 17 11 18 12 19 11 20 12 Key UGADAJMDJZPKQX CEVVSZFKBJSMILES C N1 C C2N C C C 2 C C3N C C C 3 C 4 CC C1 C C5CCC4 N 5PropertiesChemical formula C20H16N4Molar mass 312 36784Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Chlorins are excellent photosensitizing agents Various synthetic chlorins analogues such as m tetrahydroxyphenylchlorin mTHPC and mono L aspartyl chlorin e6 are effectively employed in experimental photodynamic therapy as photosensitizer 3 Contents 1 Chlorophylls 2 Variation 3 Synthetic chlorins 4 See also 5 Further reading 6 ReferencesChlorophylls editThe most abundant chlorin is the photosynthetic pigment chlorophyll Chlorophylls have a fifth ketone containing ring unlike the chlorins Diverse chlorophylls exists such as chlorophyll a chlorophyll b chlorophyll d chlorophyll e chlorophyll f and chlorophyll g Chlorophylls usually feature magnesium as a central metal atom replacing the two NH centers in the parent 4 Variation editSee also Porphyrin In nature nbsp Structures comparing porphin chlorin bacteriochlorin and isobacteriochlorin Microbes produce two reduced variants of chlorin bacteriochlorins and isobacteriochlorins Bacteriochlorins are found in some bacteriochlorophylls the ring structure is produced by Chlorophyllide a reductase COR reducing a chlorin ring at the C7 8 double boud 5 Isobacteriochlorins are found in nature mostly as sirohydrochlorin a biosynthetic intermediate of vitamin B12 produced without going through a chlorin In living organisms both are ultimately derived from uroporphyrinogen III a near universal intermediate in tetrapyrrole biosynthesis 6 Synthetic chlorins editNumerous synthetic chlorins with different functional groups and or ring modifications have been examined 7 Contracted chlorins can be synthesised by reduction of B III subporphyrin or by oxidation of corresponding B III subbacteriochlorin 8 The B III subchlorins were directly synthesized as meso ester B III subchlorin from meso diester tripyrromethane these class of compound showed very good fluorescence quantum yield and singlet oxygen producing efficiency 9 10 See also editCorrin Photodynamic therapyFurther reading editJuse lius Jonas Sundholm Dage 2000 The aromatic pathways of porphins chlorins and bacteriochlorins Physical Chemistry Chemical Physics 2 10 2145 2151 Bibcode 2000PCCP 2 2145J doi 10 1039 b000260g References edit Gerard P Moss 1988 Nomenclature of Tetrapyrroles Recommendations 1986 European Journal of Biochemistry 178 2 277 328 doi 10 1111 j 1432 1033 1988 tb14453 x PMID 3208761 Battersby Alan R 2000 Tetrapyrroles The pigments of life Natural Product Reports 17 6 507 526 doi 10 1039 b002635m PMID 11152419 Spikes John D July 1990 New trends in photobiology Journal of Photochemistry and Photobiology B Biology 6 3 259 274 doi 10 1016 1011 1344 90 85096 F PMID 2120404 K Eszter Borbas Handbook of Porphyrin Science 181 Chlorins worldscientific doi 10 1142 9789813149564 0001 ISBN 9814322326 Chew Aline Gomez Maqueo Bryant Donald A 2007 Chlorophyll Biosynthesis in Bacteria The Origins of Structural and Functional Diversity Annual Review of Microbiology 61 113 129 doi 10 1146 annurev micro 61 080706 093242 PMID 17506685 Battersby Alan R 2000 Tetrapyrroles The pigments of life A Millennium review Natural Product Reports 17 6 507 526 doi 10 1039 B002635M PMID 11152419 Taniguchi Masahiko Lindsey Jonathan S 2017 Synthetic Chlorins Possible Surrogates for Chlorophylls Prepared by Derivatization of Porphyrins Chemical Reviews 117 2 344 535 doi 10 1021 acs chemrev 5b00696 OSTI 1534468 PMID 27498781 Osuka Atsuhiro Kim Dongho 2008 Synthesis and Characterization of meso Aryl Substituted Subchlorins Journal of the American Chemical Society 130 2 438 439 doi 10 1021 ja078042b PMID 18095693 Chandra Brijesh Soman Rahul Sathish Kumar B Jose K V Jovan Panda Pradeepta K 3 Dec 2020 Meso Free Boron III subchlorin and Its m Oxo Dimer with Interacting Chromophores Organic Letters 22 24 9735 9739 doi 10 1021 acs orglett 0c03813 PMID 33270460 S2CID 227282229 Soman Rahul Chandra Brijesh Bhat Ishfaq A Kumar B Sathish Hossain Sk Saddam Nandy Sridatri Jose K V Jovan Panda Pradeepta K 15 Jul 2021 A2B and A3 Type Boron III Subchlorins Derived from meso Diethoxycarbonyltripyrrane Synthesis and Photophysical Exploration The Journal of Organic Chemistry 86 15 10280 10287 doi 10 1021 acs joc 1c01001 PMID 34264670 S2CID 235959639 Retrieved from https en wikipedia org w index php title Chlorin amp oldid 1140076524, wikipedia, wiki, book, books, library,
