-
4
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-
77952639671
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-
and references cited therein One needs to keep in mind that in the plants, reactive functional groups such as aldehydes will most likely be masked in a transitory way. In this article, in order to simplify schemes and figures, these functional groups will be shown in their reactive form. In the case of glutaraldehyde, it is a known protein-reticulating agent and its presence as a free molecule in a living cell is of course unlikely but we will see that equivalents in terms of oxidation state can be put forward (vide infra)
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A. M. Brown D. J. Robins L. Witte M. Wink Plant Physiol. (Life Sci. Adv.) 1991 10 179 185
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Plant Physiol. (Life Sci. Adv.)
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Brown, A.M.1
Robins, D.J.2
Witte, L.3
Wink, M.4
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9
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85013539502
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Atta-ur-Rahman, Elsevier, Amsterdam, pp 731-768 and references therein
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M. J. Wanner and G. J. Koomen, in Studies in Natural ProductsChemistry: Stereoselectivity in Synthesis and Biosynthesis of Lupine and Nitraria Alkaloids, ed., Atta-ur-Rahman, Elsevier, Amsterdam, 1994; vol. 14, pp 731-768 and references therein
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Studies in Natural ProductsChemistry: Stereoselectivity in Synthesis and Biosynthesis of Lupine and Nitraria Alkaloids, Ed.
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Wanner, M.J.1
Koomen, G.J.2
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13
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0031929582
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See for example:
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D. Franois M.-C. Lallemand M. Selkti A. Tomas N. Kunesch H.-P. Husson Angew. Chem., Int. Ed. 1998 37 104 105
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Angew. Chem., Int. Ed.
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Franois, D.1
Lallemand, M.-C.2
Selkti, M.3
Tomas, A.4
Kunesch, N.5
Husson, H.-P.6
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15
-
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63449112597
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-
and references cited therein. See also, ref. 5d Glutaraldehyde 2 is quite stable as an aqueous solution whereas it undergoes rapid polymerization in neat conditions with catalytic amount of water. The numerous applications of 2 have been extensively reviewed over the years as a cross-linking agent in biochemistry or histology or as a biocide: see among others
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V. C. Pham A. Jossang T. Sévenet V. H. Nguyen B. Bodo Eur. J. Org. Chem. 2009 1412 1416
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Eur. J. Org. Chem.
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Pham, V.C.1
Jossang, A.2
Sévenet, T.3
Nguyen, V.H.4
Bodo, B.5
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16
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84986905987
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Types of antimicrobials agents
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ed., A. P. Fraise, P. A. Lambert and J.-Y. Maillard, 4th edn, Blackwell Publishing, Oxford
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Types of Antimicrobials Agents, in Russel, Hugo & Ayliffe's Principle and Practice of Disinfection, Preservation and Sterilization, ed., A. P. Fraise, P. A. Lambert, and, J.-Y. Maillard, 4th edn, Blackwell Publishing, Oxford, 2004, pp. 8-97
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Russel, Hugo & Ayliffe's Principle and Practice of Disinfection, Preservation and Sterilization
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17
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0038466598
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Glutaraldehyde, in
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Cambridge University Press, Cambridge, pp. 28-42
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M. A. Hayat, Glutaraldehyde, in Principles and Techniques of Electron Microscopy, Biological Applications, Cambridge University Press, Cambridge, 2000, pp. 28-42
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Principles and Techniques of Electron Microscopy, Biological Applications
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Hayat, M.A.1
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18
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77952642333
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Glutaraldehyde, in
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John Wiley & Sons, Chichester, See inter alia:
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H.-P. Husson, J. Royer, Glutaraldehyde, in e-EROS Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 2001
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E-EROS Encyclopedia of Reagents for Organic Synthesis
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Husson, H.-P.1
Royer, J.2
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22
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33751500609
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The yield is of course low, but experimentally speaking, glutaraldehyde 2 is a cheap reagent and 6 is the most nonpolar compound of the reaction based on silica gel TLC profile which renders its purification by chomatography easy. In practise, 15 g of 2 give 3-4 g of 6 in a reproducible manner No information concerning the stereochemistry of 6 was disclosed in ref. 10. A complete study is given for the first time in the present work. Acetylation of 6 permitted the chromatographic resolution of A and B resulting from the 2 major diastereomers of 6 - see the ESI Komarovinine:
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T. Tashima M. Imai Y. Kuroda S. Yagi T. Nakagawa J. Org. Chem. 1991 56 694 697
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Tashima, T.1
Imai, M.2
Kuroda, Y.3
Yagi, S.4
Nakagawa, T.5
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25
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34249918476
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6) assignment was therefore difficult Syntheses and synthetic applications of 11 as well as other dialdehyde monoacetals have been reviewed, see:
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T. S. Tulyaganov S. Yu. Yunusov Chem. Nat. Compd. 1990 26 49 53
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(1990)
Chem. Nat. Compd.
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, pp. 49-53
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Tulyaganov, T.S.1
Yu., Y.S.2
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