ChemInform Abstract: STRUCTURAL INVESTIGATION OF THE ANTIBIOTIC RISTOMYCIN A, CHEMICAL STRUCTURE OF THE OLIGOSACCHARIDE PART OF RISTOMYCIN A

Sztaricskai, Ferenc; Bognár, R.; M, Puskás

doi:10.1002/chin.197515436

Cited by 3 publications

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“…The antibiotic ristomycin is an oligosaccharide-type compound (Sztaricskai et al 1975b, Neszmélyi et al 1978) containing a complex peptide aglycone moiety the structure of which has not been completely elucidated as yet (Katruha et al 1978a and1978b). Two primary amino, one methoxy-carbonyl, five phenolic hydroxyl and 16 hydro xyl groups of carbohydrate character were found in the ristomycin A molecule (Bognar et al 1974 a and1974b).…”

Section: A Short Characterisation Of Antibiotics Of the Vancomycin Groupmentioning

confidence: 99%

Study of Platelet Agglutination Induced by the Antibiotics of the Vancomycin Group: Ristocetin, Ristomycin, Actinoidin and Vancomycin

et al. 1979

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SummaryFour antibiotics which belong to the vancomycin group have been examined in respect of their effects on the factor VIII dependent platelet agglutination. A striking similarity between ristocetin and ristomycin was observed both in qualitative and quantitative terms, therefore ristomycin could be used to determine the so called ristocetin cofactor.Actinoidin and vancomycin inhibited platelet agglutination induced by ristocetin or ristomycin in citrate-PRP or EDTA-PRP as well as in systems containing formaldehyde- treated platelets, but did not inhibit agglutination induced by bovine factor VIII.All the four antibiotics caused plasma protein precipitation. Actinoidin was the least and vancomycin the most effective in this respect; ristocetin and ristomycin also possess this property, the effect of the latter is more considerable.Actinoidin and vancomycin did not block the immediate increase in light absorbancy in aggregometer caused by the addition of ristocetin or ristomycin to fixed platelets at concentrations which totally inhibited platelet agglutination in the presence of protein cofactor. Inhibition of this »direct effect« of ristocetin and ristomycin was observed only at higher concentrations indicating that this effect may be unrelated to the agglutination.According to our results with ristomycin derivatives the methylated carboxyl and the free phenolic hydroxyl groups may be of prime importance in the binding of ristomycin to the platelet membrane and/or to its protein cofactor. Similar data from other laboratories are confirmed and some new findings are offered.

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Section: A Short Characterisation Of Antibiotics Of the Vancomycin Groupmentioning

confidence: 99%

Study of Platelet Agglutination Induced by the Antibiotics of the Vancomycin Group: Ristocetin, Ristomycin, Actinoidin and Vancomycin

et al. 1979

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Structural investigation of the antibiotic ristomycin A. Synthesis of ristobiose and ristotriose.

Sztaricskai

Lipták²,

Pelyvás

et al. 1976

J. Antibiot.

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The antibiotic ristomycin' produced by Proactinomyces fructiferi var. ristomycini,2) and presumably identical with the antibiotic ristocetin,3) belongs to the vancomycin group of antibiotics. As shown by our investigations, ristomycin consists of the ristomycin A aglycone,4.5 whose unusual peptide structure has not been completely elucidated as yet, connected separately to one molecule of D-mannose, one molecule of ristosamine,6) and a branched heterotetrasaccharide side-chain.7) The structure of ristosamine (2,3,6-trideoxy-3-amino-L-ribo-hexopyranose) has recently been substantiated by synthesise) and this result has been confirmed by LEE and his co-workers.e)We now report the synthesis of ristobiose and ristotriose resulting from the mild acid hydrolysis of the tetrasaccharide side chain of ristomycin A.In previous studies on the sugar linkage, using permethylation followed by hydrolysis, ristobiose and ristotriose were shown to be 2-O-a-D-mannopyranosyl-D-glucose and O-a-L-rhamnopyranosylIn the present work, using the modified HELFERICH method,10) 1,3,4,6-tetra-O-acetyl-a-D-glucose (I) and a-acetobromo-D-mannose (II) were allowed to react in benzene -nitromethane (1: 1), to obtain octa-O-acetyl-a-ristobiose (III) in 74% yield (Fig. 1).glucose has recently also been synthesized by DICK et a1.11) under different reaction conditions. On the basis of the m.p., specific rotation and IR spectrum, compound III was identical in every respect with the acetylated derivative of ristobiose (IV)7) prepared from ristomycin A by mild acid hydrolysis and acetylation. The specific rotation, as well as the paper chromatographic mobility of the compound obtained after deacetylation of III by ZEMPLEN'S method" were in good agreement with the data of IV isolated from the 0.1 N hydrochloric acid hydrolyzate of the antibiotic (Table 1).For the synthesis of ristotriose (Fig. 2), hexa-O-acetyl-a-rutinosyl halide 12,11) (V: R=CHsCO: X = Cl or Br) was used as the starting material, from which hexa-O-acetyl-/3-rutinose (VII), containing a free hydroxyl group at C-2, was obtained by the method of HELFERICH and ZIRNER.14) As a result of the nucleophilic attack of acetate ion on compound V (prepared in both ways) in aqueous acetic acid, hepta-O-acetyl-a-rutinose (VI) was formed as the main product in 56 % yield. The hexa-O-acetyl-

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Structural investigation of the antibiotic ristomycin A. The amino acid constituents.

Sztaricskai

Harris

1979

J. Antibiot.

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Hydrolysis of the O-methylated aglycone of ristomycin A by a mixture of KOH and NaBH4 yielded a mixture of aromatic amino acids which, after N-acetylation and Ome.hylation, were separated by chromatography on silica gel. Compounds III' VII were isolated and identified by pmr and mass spectroscopy.Compounds V -VII were also oxiiatively degraded to the corresponding benzoate esters. Compounds III and IV are derived from ristomycinic acid (I) and V from actinoidinic acid (II), both of which had been obtained in earlier acid hydrolyses of the antibiotic.Compounds VI and VII had not been detected previously nor glycine which was also found to be a product of base hydrolysis. It is postulated that the new products arise from bisdechlorovancomycinic acid (X). It is concluded that aglycoristomycin A comprises I, II and X which also corstitute the aglycone of ristocetin A.

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ChemInform Abstract: STRUCTURAL INVESTIGATION OF THE ANTIBIOTIC RISTOMYCIN A, CHEMICAL STRUCTURE OF THE OLIGOSACCHARIDE PART OF RISTOMYCIN A

Cited by 3 publications

References 0 publications

Study of Platelet Agglutination Induced by the Antibiotics of the Vancomycin Group: Ristocetin, Ristomycin, Actinoidin and Vancomycin

Study of Platelet Agglutination Induced by the Antibiotics of the Vancomycin Group: Ristocetin, Ristomycin, Actinoidin and Vancomycin

Structural investigation of the antibiotic ristomycin A. Synthesis of ristobiose and ristotriose.

Structural investigation of the antibiotic ristomycin A. The amino acid constituents.

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