Antibiotic Yc 73 of Pseudomonas Origin. Iii

Ito, Yukio; Umino, Kimio; Sekiguchi, Toshio; Miyagishima, Toshikazu; Egawa, Yoshiyuki

doi:10.7164/antibiotics.24.131

Cited by 13 publications

(8 citation statements)

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“…However, diphosphorus decasulfide with hydroxamic acids gives a complex mixture of products, among which thiohydroxamic acids are present only in small quantities. Hence, this reaction cannot be classified as a good synthetic method [65,66].…”

Section: Reactions Of Direct Thionation Of Hydroxamic Acids and Theirmentioning

confidence: 99%

The thiohydroxamate system

Chimiak

Przychodzeń

Rachoń

2002

Heteroatom Chemistry

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Section: Reactions Of Direct Thionation Of Hydroxamic Acids and Theirmentioning

confidence: 99%

The thiohydroxamate system

Chimiak

Przychodzeń

Rachoń

2002

Heteroatom Chemistry

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“…Also the synthesis of Nhydroxythiopeptides has recently begun to attract considerable attention [3]. Unfortunately, thionation with P 4 S 10 produces complex mixtures containing only small quantities of the desired THAs [4,5]. Rzepa and coworkers [6] proposed an approach that involved a three-step procedure with protection and deprotection of the N OH moiety during the synthesis of THAs using Lawesson's reagent (LR), but yields of the corresponding THAs 2 were low (10-50%), probably because of lability of Oacetylthiohydroxamic acids.…”

Section: Introductionmentioning

confidence: 99%

Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity

Przychodzeń

2006

Heteroatom Chemistry

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To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic ␣-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated withBrown sigma parameter. The relative rates of two subsequent processes k T 2 and k R 2 were also measured. Correlation was also found for methine proton chemical shifts of N-isopropyl benzothiohydroxamic acids.

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“…Miyagishima demonstrated earlier that N-substituted formohydroxamate complexes are not inhibitory, whereas N-substituted thioformohydroxamate complexes of iron(III) are (4,12). The antibiotic activity of hydroxamate complexes might be precluded, since this functional group is responsible for the coordination of iron(III) in a number of iron(III) transport agents manufactured by microorganisms under iron-deficient conditions (14).…”

Section: Tris([3s]n-methylthioformohydroxamato)iron-mentioning

confidence: 99%

“…These naturally occurring antibiotics have been isolated from the culture supernatant fluids of Pseudomonas (1,10,16) and Streptomyces species (S. Miyamura, Japan Patent 87087, 1973). Ferric complexes of chemically synthesized N-substituted thioformohydroxamiic acids, which are analogs of thioformin (N-methylthioformohydroxamic acid), also exhibit antibiotic activity against bacteria such as Staphylococcus aureus 209P and Escherichia coli NIHJ, and fungi such as Candida albicans Eiken (2,4,12).…”

mentioning

confidence: 99%

Antibiotic Action of N -Methylthioformohydroxamate Metal Complexes

Bell

Friedman

Leong

1979

Antimicrob Agents Chemother

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The antibiotic activity of metal complexes of N-methylthioformohydroxarnic acid against gram-negative Escherichia coli NIHJ and gram-positive Staphylococcus aureus 209P was investigated. 'The kinetically labile, square-planar, divalent (Cu, Ni, and Pd) and octahedral, trivalent (Fe, Co, and Cr) complexes displayed activity, whereas the more inert platinum(II) or rhodium(III) complex displayed no activity, or activity only at elevated concentrations. The free ligand did not suppress the growth of the above organisms, and the sulfur atom of the ligand in its metal complexes appears crucial for activity. Uptake studies of radioactively labeled N-methylthioformohydroxamic acid, its nickel(II), platinumn(II), iron(III), and rhodium(III) complexes were conducted in the Escherichia coli K-12 RW193 mnutant, which is defective in the production of its native iron(III) transport agent, enterobactin. Uptake of "'Fe or "Ni label from their metal complexes appeared to occur as free inorganic metal ions. The antibiotic activity of the iron(III) and nickel(II) complexes was not due merely to an enhanced accumulation of nietal ions by the cell. Metal complexes of [;"S]Nmethylthiofotnohydroxamic acid enhanced the accumulation of 3"S label compared to that of the free ligand. The antibiotic activity and uptake data are discussed in terms of possibls modes of action.

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Antibiotic Yc 73 of Pseudomonas Origin. Iii

Cited by 13 publications

References 0 publications

The thiohydroxamate system

The thiohydroxamate system

Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity

Antibiotic Action of N -Methylthioformohydroxamate Metal Complexes

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