Butirosins A and B, aminoglycoside antibiotics. III. Structures

Pseudosaccharides containing various natural combinations of rings present in aminoglycoside antibiotics were prepared from the parent antibiotics, neomycin B, paromomycin, and lividomycin B, by oxidation of available vicinal diols and β-elimination. Pseudotrisaccharides comprising rings A, B, and C of paromomycin and lividomycin B, a pseudotrisaccharide comprising rings B, C, and D of the three antibiotics, and a 'core' pseudotrisaccharide containing rings B and C were thus prepared. These are valuable biological probes and intermediates for semisynthetic work in this series.

supporting

confidence: 76%

Aminoglycoside antibiotics: Chemical conversion of neomycin B, paromomycin, and lividomycin B into bioactive pseudosaccharides

Hanessian¹,

Takamoto²,

Massé³

et al. 1978

“…anline (18) after column chromatography on Dowex I -X2 hydroxide form ion-exchange resin in an overall yield of 261; froill 1,3-di-AT-benzyloxycarbonyl deoxystreptamiiie (2). The white solid thus obtained as homogeneous when examined by paper chronlatography and paper electrophoresis.…”

Section: S Y~~r I~e S I S Qf'46-di-o-x-~-gl~icop~~rar~osyl-deox~~-mentioning

confidence: 99%

“…The deoxystreptamine antibiotics include the kanamycins A, B, and C, the neort~ycins A, B, and C, the paromoruycins I and 11, the gentamycins, hygromycin B,, the nebramycins (see ref. 1 for a review of the foregoing antibiotics), butyrosins ( 2) , destomycin A (3), and sisomycin (4). In many of these antibiotics at least one of the glycosidic bonds to the deoxystreptamine residue involves an a-D-gluco-linkage with or without an amino group at the 2-position.…”

mentioning

confidence: 99%

“…Syntlzeses of Molzo-0-a-D-glucoyj~raiiosyl Dericat i x s of Deoxystreytanzine The 1,3-di-N-benzyloxycarbonyl derivative of deoxystreptamine (2) has been reported (1 9) to be a suitable derivative of deoxystreptailii~le for the syntllesis of a varicty of its 0-glycosides. Thc good solubility of 2 in diinethylformamide and the ease of removai of the protecting groups by catalytic hydrogenation appeared in our hands also to be superior to other possible derivatives.…”

mentioning

confidence: 99%

See 1 more Smart Citation

The Synthesis of Kanamycin Analogs I. α-D-Glucopyranosyl Derivatives of Deoxystreptamine

Lemieux¹,

Nagabhushan²,

Clemetson³

et al. 1973

The procedure developed in this laboratory for the synthesis of ci-D-glucopyranosides based on the reaction of dimeric tri-0-acetyl-2-deoxy-2-nitroso-a-D-glucopyranosy chloride with alcohols was employed to synthesize the three cc-D-glucopyranosyl deoxystreptamines and 4,6-di-0-a-D-glucopyranosyl deoxystreptamine. Effects of p H change on the n.m.r. spectra of kananiycins A and B and of the above synthetic compounds are interpreted in terms of a conforniational change.Le procede developpi au laboratoire pour la synthese des .*-D-glucopyranosides a partir de la reaction entre le chlorure de tri-0-acttyl-dCoxy-2 nitroso-2-r-D-glucopyranosyle dimere et les alcools, a kt6 utilise pour obtenir les trois r-D-glucopyranosyl deoxystreptamines et le di-0-r-D-glucopyranosyl-4,6-deoxystreptamine. Les effets du p H sur les spectres r.m.n. des kanamycines A et B des composes synthitiques ci dessus sont interpretes par rapport au changement conformationnel.

“…Unlike its positional isomer 6, pseudotrisaccharide 13 was found to be inactive against a variety of gram-positive and gram-negative strains in a standard antibacterial assay.2 Interestingly it was also found t o be a good substrate for phosphotransferases I and 11, elizynies which are known to inactivate aminoglycoside antibiotics by phosphorylation at the C-3'-hydroxyl group (21). 3 As previously mentioned, seenlingly minor peripheral modifications in the basic niolecular architecture of the anlinoglycoside ~nolecule may have profound effects 011 their biological properties. Since neamine was known to be a Inore effective inhibitor of the in vitro growth of bacteria than its 6'-hydroxy analog paronianiine, it was of interest to convert the pseudotrisaccharide 13 into its neamine counterpart, i.e.…”

mentioning

confidence: 97%

Aminoglycoside antibiotics: Synthesis of pseudotrisaccharides derived from neamine and paromamine

Hanessian¹,

Ogawa²,

Takamoto³

1978

Pseudotrisaccharides of paromamine having a 6-O-(β-D-ribofuranosyl) and 6-O-(α-D-arabinofuranosyl) moieties were prepared from appropriately N,O-substituted derivatives of paromamine by glycosylation reactions. Selective functionalization at C-6′ in 6-O-(β-D-ribofuranosyl)paromamine led to the corresponding neamine-containing pseudotrisaccharide. None of these semisynthetic aminoglycosides possessed antibacterial activity, although at least one of them has been shown to be a substrate for the phosphotransferases I and II. The unnatural attachment of a pentofuranosyl moiety at C-6 of the 2-deoxystreptamine unit in these pseudotrisaccharides is, therefore, detrimental to their antibacterial action, unlike amino sugar containing analogs at the same position.