By R. Bangert, J. Bonner, H. Brockmann, L. Crombie, L. Jaenicke, C. Kutzbach, A.D. Mebane, H. Muxfeldt, W. Oroshnik
ISBN-10: 3709171490
ISBN-13: 9783709171493
ISBN-10: 3709171504
ISBN-13: 9783709171509
In the course of the early 1950's there seemed stories, now and then of the presence one of the items elaborated by means of actinomycetes of antifungal antibiotics which exhibited very comparable and extremely attribute multipeaked ultraviolet absorption spectra. In 1954, with a great number of examples on list, those spectra have been analyzed and pointed out as these of straight-chain conjugated polyenes, comprising tetraenes, pentaenes, hexaenes and heptaenes (85, I30). those antibiotics have considering the fact that been quite often known as the polyene antifungal antibiotics to differentiate them from a number of different miscellaneous antibiotics which even have antifungal houses. in the following few years, reviews of discoveries of recent individuals of this type extended speedily, and nearly sixty at the moment are recognized. undoubtedly, a few those will ultimately be came across to be exact with others, as has already occurred in different cases: for instance, the tetraene "tennecetin" proved to be a rediscovery of pimaricin (34), and within the methyl- pentaenes "moldcidin E" has been pointed out with pentamycin (83), and "lagosin" seems to be indistinguishable from fungichromin (22). those who were purified have became out to be of quite excessive molecular weight (ca. 700-1300) and all seem to be components of particularly related molecular constitution. up to now purely 3, pimaricin, fungi- chromin (lagosin) and filipin, were structurally elucidated.
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Sample text
32) on the hypothesis, which was nearly correct, that filipin would prove to be deoxy-"lagosin". -acyloxy groups in the fully acetylated derivative (35). As with "lagosin", alkali treatment freedhexanaldehyde (I3) , indicating an aldolic side-chain which (for lack of any other carbonyl group) must necessarily be iX- to the lactone. Although the filipin chromophore is clearly the same as that of fungichromin, a difference in its environment is indicated by the facile selective removal of the terminal trisubstituted double bond with uptake of one oxygen atom [e.
Or HOCHz-CH-CH-CHs I I o OH I -c=o I,z-Propanediol. ) 2L: 3D (erytkYo)I,Z,3-Butanetriol. ) Chart 3. Identification of the Esterified Hydroxyl Group in Fungichromin. An interesting further point is that the propylene glycol was found to be optically active (D-enantiomer). By repeating the reactions with omission of the periodic acid treatment, compound (XIV) was obtained in 45 % yield, thus establishing the configuration of these two hydroxyls. Although all of this work was done on perhydrofungichromin, there is no ambiguity about the nature and location of the chromophore, which the M.
TigIic aldehyde. Chart 5. Oxidative Fission of Nystatin. Kuhn-Roth oxidation showed the presence of four C-methyl groups, all of which are accounted for by the above fragments (two in tiglic aldehyde, one as the branch-methyl in the C1s-dibasic acid, and one in mycosamine). How the moieties should be connected is as yet uncertain, but (XXIX) has been suggested (36), with a ring-closing chain containing only non-vicinal hydroxyls (one of which is primary) and a carboxyl, tentatively formulated as in (XXX).
Progress in the Chemistry of Organic Natural Products/Progres Dans La Chimie Des Substances Organiques Naturelles by R. Bangert, J. Bonner, H. Brockmann, L. Crombie, L. Jaenicke, C. Kutzbach, A.D. Mebane, H. Muxfeldt, W. Oroshnik
by Robert
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