398. 2,3,4,6-Tetra-O-benzyl-<scp>D</scp>-glucosyl chloride and its use in the synthesis of the α- and β-anomers of 2-O-<scp>D</scp>-glucosylglycerol and 4-O-<scp>D</scp>-glucosyl-<scp>D</scp>-ribitol

Austin, P. W.; Hardy, F. E.; Buchanan, J. G.; Baddiley, J.

doi:10.1039/jr9640002128

Cited by 74 publications

(18 citation statements)

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“…Viridicatol was isolated previously along with viridicatin from a strain of P. viridicatin [23]. Functionalized 4-arylquinolin-2(1H)-ones constitute generally, a valuable class of biologically active molecules, including several fungal metabolites such as viridicatin [24] and 3-Omethylviridicatin [25]. Viridicatol was reported to show cytotoxicity toward KB, KBv200, A549, …”

Section: Viridicatol (1)mentioning

confidence: 99%

Bioactive Compounds Produced by Strain of Penicillium sp.

Shaaban¹,

Sohsah²,

El-Metwally³

et al. 2016

IJSEA

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During our search for bioactive compounds from fungi, the terrestrial Penicilliumsp.KH Link 1809 isolate KHMM was fermented on large scale using solid rice medium. After harvesting, working up and purification of the afforded extract using different chromatographic techniques, the bioactive metabolites viridicatol (1) and kojic acid (2) were isolated. The chemical structures of 1 and 2 were confirmed by extensive 1D and 2D NMR and mass measurements, and by comparison with literature data. The antimicrobial activity of the strain extract was studied using a panel of pathogenic microorganisms.

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Section: Viridicatol (1)mentioning

confidence: 99%

Bioactive Compounds Produced by Strain of Penicillium sp.

Shaaban¹,

Sohsah²,

El-Metwally³

et al. 2016

IJSEA

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“…Paromamine (17) is a constituent of kanamycin C (1 0), paromomycins (5,6), and many others. Neomine (19) is a constituent of neomycins (3,4) (14); the total yield of a-glycosides was 85% and, since (14) was a racemate, the desired 4-0-and 6-0-a-glycosyl compounds (15,16) were obtained in yields of 49 and 36%, respectively. Neomine (19) was derived from paromamine by selective tosylation of its primary hydroxyl group followed by azide displacement and catalytic reduction (Ref.…”

Section: Ho Ohmentioning

confidence: 99%

Recent advances in the synthesis of aminoglycoside antibiotics

Umezawa¹

1978

Pure and Applied Chemistry

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Abstract-Aminoglycoside antibiotics have established an important position in medicine and synthetic chemistry in this field has recently been developed. A review is provided of general synthetic schemes which we have developed for the total synthesis of streptomycin, dihydrostreptomycin, kanamycins, butirosin B, neomycin C, and others. Resistent bacteria are a serious subject in present chemotherapy and, the mechanisms of resistance have recently been revealed by medical microbiologists. ln the light of these mechanisms, an effort has been made to synthesise compounds, active against resistent bqcteria, by extension of the above mentioned synthetic schemes and by derivation from natural antibiotics.

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“…No glucosidation of 2 was achieved under halide ion catalyzed conditions using bromide 14 (21). Therefore, the glucosidation was carried out with chloride 3 (22) and mediated by silver trifluoromethanesulfonate at -10°C to produce an a : p-mixture of 4 and 5 in the ratio 3.5 : 1. Repeated column chromatography provided the a-anomer 4 in 66% and the p-anomer 5 in 19% yield.…”

Section: Synthesismentioning

confidence: 99%

Inhibitors of endo-α-mannosidase. Part II. 1-Deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin and congeners modified in the mannojirimycin unit

Spohr¹,

Bach²,

Spiro³

1993

Can. J. Chem.

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The syntheses of 1-deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin (9) and its 2-deoxy, 2-O-methyl, 4-deoxy, 4-O-methyl, 6-deoxy, 6-O-methyl, N-methyl, and N-propyl congeners are described. Since 9 was previously shown to effectively inhibit endo-α-D-mannosidase, a glycoprotein-processing hydrolase, these chemical modifications were designed to assist in the assessment of intermolecular hydrogen bonds of the inhibitor–enzyme complex. The previously reported data require that all hydroxyl groups of the deoxymannojirimycin unit of 9, namely, OH-2, OH-4, OH-6, and also the NH-5 group, interact with charged and polar groupings of the enzyme, since deoxygenations and alkylations abolished or significantly reduced activities. Conformational analysis of 9 and some of its congeners based on NMR chemical shifts, experimental and theoretical nuclear Overhauser enhancements, and HSEA calculations were performed. The chemical modifications of the glucose unit of 9 are described in the accompanying paper.

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398. 2,3,4,6-Tetra-O-benzyl-D-glucosyl chloride and its use in the synthesis of the α- and β-anomers of 2-O-D-glucosylglycerol and 4-O-D-glucosyl-D-ribitol

Abstract: Tetra-O-benxyl-~-glucosyl Chloride and i t s Use in the Synthesis of the a-and p-Anomers of 2-O-~-Glucosylglycerol and ~-O -D -ClUCOsyl-D -YibitOl.

Cited by 74 publications

References 0 publications

Bioactive Compounds Produced by Strain of Penicillium sp.

Bioactive Compounds Produced by Strain of Penicillium sp.

Recent advances in the synthesis of aminoglycoside antibiotics

Inhibitors of endo-α-mannosidase. Part II. 1-Deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin and congeners modified in the mannojirimycin unit

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