Olivomycin and related antibiotics XXX. The structure of chromocyclin

Summary 1. The glycoside chromocyclomycin has been isolated from the culture liquid ofStreptomyces LA-7017, and its aglycone, chromocyclin, has been obtained.2. As a result of degradation and the results of a comparison with the properties of model compounds, structure (I) has been established for chromocyclin.For a preliminary communication see [1]; for Communication XXIX, see [2].M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 524–532, July–August, 1973.     

Olivomycin and related antibiotics XXV. Stereochemistry of the side chain of olivin

Summary The configurations of the C₃ and C₄ centers of olivin have been shown by the oxidative cleavage of olivin penta- and hexaacetates (V) and (VI) with the formation of D-acetyllactic and D-threo-dihydroxy-butyric acids (VIII) and (IX). The stereochemistry of the C₁ center has been determined by the spectropolarimetric correlation of the products of the degradation of olivin (XVI)–(XVIII) with the model substances (XXII)–(XXIV). As a result, the 2S, 3R, 1S, 3S, 4R configuration has been established for olivin.For Communications XXIII and XXIV, see [1, 2]; for a preliminary communication, see [3].M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 519–525, July–August, 1972.     

Olivomycin and related antibiotics

Conclusions It has been shown that olivomose, which forms part of the carbohydrate moiety of olivomycins A, B, C, and D, possesses the structure of 4-O-methyl-2, 6-dideoxy-D-lyxo-hexose (VI).Khimiya Prirodnykh Soedinenii, Vol. 5, No. 2, pp. 103–109, 1969     

Olivomycin and related antibiotics

Summary It has been shown that olivomycose has the structure of 3-C-methyl-2, 6-dideoxy-L-arabino-hexose. In olivomycins A and C, this sugar is present in the form of the 4-O-isobutyrate, and in olivomycin B in the form of the 4-O-acetate.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 6, pp. 405–410, 1967For preliminary communication, see [1].     

Olivomycin and related antibiotics

Summary 1. From the culture fluid of the ray fungusActinomyces olivoreticuli four individual antibiotics, olivomycins A, B, C, and D have been isolated.2. The acid degradation of olivomycins A, B, C, and D has been carried out with the formation of the aglycone olivin and the carbohydrates olivomycose, olivomose, olivose, oliose, and (or) their derivatives.3. The qualitative and quantitative monomeric composition of olivomycins A, B, C, and D has been elucidated and their empirical formulas have been established.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 5, pp. 331–339, 1967For previous communications, see [1]; for Communication IX, see [2].     

Olivomycin and related antibiotics

Conclusions It has been shown that the five monosaccharide residues forming the carbohydrate moiety of the antibiotic olivomycin A form two unbranched chains attached to the hydroxyls in positions 2 and 6 of the aglycone and terminated by isobutyrylolivomycose and olivomose.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 6, pp. 561–566, 1969For a preliminary communication, see [1], and for part XVI, see [2].     

Olivomycin and related antibiotics

Conclusions On the basis of its chemical properties and spectral characteristics, structure I has been established for the aglycone of the olivomycin antibiotics, olivin.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 304–316, 1969For part XIII, see [1], and for a preliminary communication, see [2]. The subject matter of the present paper was presented in part at the International Congress on Antibiotics (Prague, 1964), and at the IX-th Mendeleev Conference on General and Applied Chemistry (Kiev, 1965).     

Olivomycin and related antibiotics XXVI. The absolute configurations of olivin and of chromomycinone

Summary The stereochemical correlation of olivin with chromomycinone and the directed degradation of the first of them to di-O-methyl-D-tartaric acid (XXI) has been effected. As a result, it has been shown that olivin and chromomycinone both have the absolute configuration 2S,3R,1S,3S,4R and possess the respective structures (Ia) and (Ib).For Communication XXV, see [1], and for a preliminary communication see [2].M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 526–534, July–August, 1972.     

Olivomycin and related antibiotics XXVIII. Monomeric composition of aureolic acid and proof that the antibiotics LA-7017 and mithramycin are identical to it

Summary 1. It has been shown that aureolic acid, antibiotic LA-7017, and mithramycin are identical.2. It has been established that aureolic acid is a glycoside of chromomycinone (I) and contains the monosaccharides D-olivose (II), D-oliose (III), and D-mycarose (IV) in a ratio of 3 : 1 : 1.For Communication XXVII, see [1], and for a preliminary communication see [2].M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. All-Union Scientific-Research Institute of Antibiotics. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 537–541, July–August, 1972.