Structure of hygromycin B, an antibiotic from <i>Streptomyces hygroscopicus</i>; The use of CMR. spectra in structure determination, I

Neuss, Norbert; Koch, Kevin; Molloy, Bryan B.; Day, W. A.; Huckstep, L. L.; Dorman, Douglas E.; Roberts, John D.

doi:10.1002/hlca.19700530846

Cited by 49 publications

(16 citation statements)

References 9 publications

(2 reference statements)

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“…AGENTS CHEMOTHER. (26) ished that the phosphate resided on the 4-xyl group adjacent to the methylamino at C-3 rather than on the 6-hydroxyl group nt to the primary amino group at C-1. The ct of modification is thus 4-0-phosphoryl-'he site of modification is indicated by the in Fig.…”

Section: Resultsmentioning

confidence: 93%

Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli

Rao¹,

Allen²,

Hobbs³

et al. 1983

Antimicrob Agents Chemother

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Section: Resultsmentioning

confidence: 93%

Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli

Rao¹,

Allen²,

Hobbs³

et al. 1983

Antimicrob Agents Chemother

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“…It has a dual ether linkage between its second and fourth rings, forming a third ring ( Fig. 1; Neuss et al 1970;Sutcliffe 2005). Other structurally related aminoglycosides such as neomycin, paromomycin, and gentamicin possess 4,5-substituted and 4,6-substituted 2-deoxystreptamine (2-DOS) cores which form ring II of the drugs, and a glucosamine sugar, or ring I, attached at position 4 in ring II (Fig.…”

Section: Introductionmentioning

confidence: 99%

Structural basis for hygromycin B inhibition of protein biosynthesis

Borovinskaya¹,

Shoji²,

Fredrick³

et al. 2008

RNA

105

102

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Aminoglycosides are one of the most widely used and clinically important classes of antibiotics that target the ribosome. Hygromycin B is an atypical aminoglycoside antibiotic with unique structural and functional properties. Here we describe the structure of the intact Escherichia coli 70S ribosome in complex with hygromycin B. The antibiotic binds to the mRNA decoding center in the small (30S) ribosomal subunit of the 70S ribosome and induces a localized conformational change, in contrast to its effects observed in the structure of the isolated 30S ribosomal subunit in complex with the drug. The conformational change in the ribosome caused by hygromycin B binding differs from that induced by other aminoglycosides. Also, in contrast to other aminoglycosides, hygromycin B potently inhibits spontaneous reverse translocation of tRNAs and mRNA on the ribosome in vitro. These structural and biochemical results help to explain the unique mode of translation inhibition by hygromycin B.

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“…The formed aminopyrans 17a and 17b can be regarded as amino C -glycosides. Compound 17a is related to compounds with β-D-talose configuration that are rarely found in nature, an exception being the antibiotic amino glycoside hygromycin B [37]. Aminopyran 17b correlates to β-D-idopyranose; iduronic acid is a component of sulfated glycosamine glycans such as chrondroitin sulfate and heparan sulfate [38].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

Kandziora¹,

Reißig²

2014

Beilstein J. Org. Chem.

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SummaryAn approach to β-D-2-aminotalose- and β-D-2-aminoidose-configured carbohydrate mimetics bearing a phenyl substituent is described. Unnatural divalent rigid p-terphenyl-linked C-aryl glycosides with 2.0 nm dimension are available using Suzuki cross-couplings. The key compound, a p-bromophenyl-substituted 1,2-oxazine, was prepared by a stereoselective [3 + 3]-cyclization of a D-isoascorbic acid-derived (Z)-nitrone and lithiated TMSE-allene. The Lewis acid-induced rearrangement of this heterocycle provided the corresponding bicyclic 1,2-oxazine derivative that may be regarded as internally protected amino sugar analogue. After subsequent reduction of the carbonyl group, the resulting bicyclic compound was used for Suzuki cross-couplings to form biphenyl aminopyran or p-terphenyl-linked dimers. Hydrogenolysis afforded new unnatural aminosugar mimetics. Zinc in the presence of acid or samarium diiodide were examined for the N–O bond cleavage in order to obtain the rigid p-terphenyl-linked C-glycosyl dimers.

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Structure of hygromycin B, an antibiotic from Streptomyces hygroscopicus; The use of CMR. spectra in structure determination, I

Cited by 49 publications

References 9 publications

Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli

Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli

Structural basis for hygromycin B inhibition of protein biosynthesis

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

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