Hydroxy streptomycin

Genes coding for NDP-hexose synthetases and NDP-hexose 4,6-dehydratases have been found in the clusters of the antibiotics granaticin (10) [122], streptomycin (24) [72], hydroxy-streptomycin [72], amphotericin [103], tylosin (46) [143], daunomycin (29) [144], lincomycin [145], landomycin A (12) and urda-... 

Folkers and coworkers - found that when sufliciently pure concentrates of streptomycin were treated with methyl orange (the sodium salt of helianthine) a crystalline salt was formed with the sulfonic acid group of this dye. On recrystallization from aqueous methanol, pure streptomycin helianthate was obtained. The helianthate could be converted to streptomycin hydrochloride, sulfate or any other suitable salt for chemical or therapeutic purposes. All of these salts with the common inorganic acids are amorphous. They - also obtained a crystalline salt of streptomycin and p-(2-hydroxy-l-napthylazo)-benzenesulfonic acid from streptomycin hydrochloride and the azo dye Orange II. Streptomycin helianthate was converted directly into a crystalline streptomycin trihydrochloride-calcium chloride double salt. The chemistry of streptomycin was thus put on a crystalline basis. 

Variations of the Structure of Natural Cord-factor in Different Strains. —It is known that different strains frequently contain a different assortment of mycolic acids. Thus, it is not astonishing that cord factor of different strains sometimes contains different mycolic acids. It was found that cord factor of a streptomycin-resistant strain of H37-Rv and of the BCG strain contains a methoxyl-free 3, x-dihydroxymycolanoic acid C87H174O4 5 CHj, whereas the virulent, human strain Br vannes contains a cord factor wherein the mycolic acid is a 3-hydroxy-x-methoxy-mycolanoic acid C88H176O4 5 CH2. 

It is worthy of note that the substance maltol, 2-methyl-3-hydroxy-7-pyrone, which is related to XLII, occurs in pine needles along with L-ascorbic acid. This substance maltol, however, is not a growth promoter like L-ascorbic acid but an inhibitor, a point of interest inasmuch as it has been obtained in considerable quantity by the degradation of streptomycin. Since the naturally occurring para-ascorbic acid or hexenolactone, also a derivative of a-pyrone, is known to display anti-growth properties, it is not unlikely that other analogs of ascorbic acid may be growth inhibitors. 

Hygromycin A [1] is classified chemically as a member of the aminocyclitols antibiotic family represented by streptomycin and kanamycin. Its structure determined by degradation and spectral analyses, (72, 13) revealed that it consists of three unusual moieties, namely S-dehydro-a-L-fucofuranose, ( )-3-(3,4-dihydroxyphenyl)-2-methylacrylic acid, and an aminocyclitol (2L-2-amino-2-deoxy-4,5-0-methylene- eo-inositol). The 5-dehydro-a-L-fucofuranose moiety is attached by a glycosidic linkage of the 4-hydroxy position of ( )-3-... 

Maltol 3-Hydroxy-2 methyl-4H pyran-4-one 3-hydroxy-2-methyl-4-py rone 3-hydroxy-2-methyl- y-py-rone larixinic acid Palatone Veltol. C6H603 mol wt 126,11. C 57.14%, H 4.80%, O 38.06%. Found in the bark of young larch trees (Larix decidua Mill.) in pine needles (Abies alba Mill., Pinaoeae), in chicory, in wood tars and oils, in roasted malt. Isoln from these sources and structure Kiliani, Bazlen, Ber. 27, 3115 (1894) Feuerstein, Ber. 34r 1804 (1901) Erdmann, Schaefer, Ber. 43, 2398 (1910) Reichstein. Be it ter, Ber. 63, 824 (1930) cf. Pera toner, Tam-burelic, Chem. Zentr. 76, 11 680 (1905). Also obtained by alkaline hydrolysis of streptomycin salts Schenck, Spiel -... 

Phenolic constituents of M grandiflora L., namely magnolol (6), honokiol (7), and 3, 5 -diallyl-2 -hydroxy-4-methoxy-biphenyl (46) were found to have good antibacterial activity against Bacillus subtilis. Staphylococcus aureus, and Mycobacterium smegatis when compared to streptomycin sulfate [67]. Additionally, magnolol and honokiol were found to be... 

That the aldehydo-group of streptomycin does not cyclize with either the methylamino- or the guanidino-groups to form a four-ring structure has been shown by n.m.r. spectroscopy. Instead it is suggested that the group is probably hydrated and stabilized by the C-3 hydroxy-group of L-streptose, ... 

Beyer S, Distler j, Piepersberg W. The str gene Chester for the hinaynthesis of 5 hydroxy-streptomycin in Srreptomyces glaucescens GLA.O (ETH 22794) New operons and evidence for pathway-specific regulation by StrR. Mol Gen Genet 1996 250 775-784. 

When subjected to alkaline hydrolysis streptomycin yields maltol, 2-methyl-3-hydroxy-y-pyrone, quantitatively and this fact may be used in the assay of streptomycin, the maltol being determined either spectro-photometrically (maximum absorption at 322 m//) or colorimetrically (after reaction with ferric iron to give a purple-red colour). Dihydrostreptomycin will not yield maltol under the conditions given below so that streptomycin can be determined in its presence as, for example, in Streptoduocin for Injection, U,S.P, which contains equal amounts of the two antibiotics. 

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