MJ347-81F4 A &amp; B, Novel Antibiotics from Amycolatopsis sp.: Taxonomic Characteristics, Fermentation, and Antimicrobial Activity.

Sasaki, Tōru; Otani, Toshio; Matsumoto, Hiroshi; Unemi, Norio; Hamada, Masa; Takeuchi, Tomio; Hori, Makoto

doi:10.7164/antibiotics.51.715

Cited by 72 publications

(47 citation statements)

References 19 publications

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“…Significant advances in biology and chemistry have taken place since then. Upon closer examination of this chemical class, compounds such as glycothiohexide a [10,11], S54832A-I [7], MJ347-81F4A and B [12] and nocathiacins [13,14] appeared more attractive than the rest because they contained aminoglycosidic residue, which inherently provided potential for improvement of aqueous solubility. This was illustrated by chemical modifications of nocathiacin I [13ϳ23].…”

Section: Isolation and Structure Elucidation Of Thiazomycinmentioning

confidence: 99%

Isolation and Structure Elucidation of Thiazomycin

et al. 2007

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Thiazolyl peptides are a class of rigid macrocyclic compounds richly populated with thiazole rings. They are highly potent antibiotics but none have been advanced to clinic due to poor aqueous solubility. Recent progress in this field prompted a reinvestigation leading to the isolation of a new thiazolyl peptide, thiazomycin, a congener of nocathiacins. Thiazomycin possesses an oxazolidine ring as part of the amino-sugar moiety in contrast to the dimethyl amino group present in nocathiacin I. The presence of the oxazolidine ring provides additional opportunities for chemical modifications that are not possible with other nocathiacins. Thiazomycin is extremely potent against Gram-positive bacteria both in vitro and in vivo. The titer of thiazomycin in the fermentation broth was very low compared to the nocathiacins I and III. The lower titer together with its sandwiched order of elution presented significant challenges in large scale purification of thiazomycin. This problem was resolved by the development of an innovative preferential protonation based one-and/or two-step chromatographic method, which was used for pilot plant scale purifications of thiazomycin. The isolation and structure elucidation of thiazomycin is herein described.

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Section: Isolation and Structure Elucidation Of Thiazomycinmentioning

confidence: 99%

Isolation and Structure Elucidation of Thiazomycin

et al. 2007

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“…7 Although rare, the 1-hydroxyindole structure is found in living organisms. [11][12][13] Particularly, the occurrence of 1-hydroxytryptophan and 1-hydroxytryptamine in living organisms imply the significance of 1-hydroxyindoles. 8 Furthermore, biological studies have shown that 1-hydroxyindoles have substantial biological activities including antiproliferative 14 and platelet aggregation inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 3-[(alkylthio)methyl]-1-hydroxy-2-(4'-substituted phenyl)indoles and their mechanistic studies on substituent effects

Cho¹,

Kim²,

Lim³

et al. 2017

Arkivoc

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The synthesis and mechanistic studies of new 3-[(alkylthio)methyl]-1-hydroxy-2-(4'-substituted phenyl)indoles 1 were presented. New substrates 2 were prepared by the application of efficient three-step synthesis with minor modifications, and used to produce target 1-hydroxyindoles 1. Substrates 2 were reacted with thiol nucleophiles in the presence of SnCl2·2H2O and 4Å molecular sieves to afford sixteen novel 1-hydroxyindoles 1, by a consecutive process involving nitro reduction, intramolecular cyclization, and nucleophilic 1,5-addition. Studies on the mechanistic aspects of these reactions with focus on the effects of p-substituent (X) in phenyl ring at C(1) in 2 were performed.

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“…4 or Amycolatopsis sp. 5 They possess excellent in vitro potency against multiple resistant strains of Gram-positive bacteria, including PRSP, MRSA and VRE. This class of natural products act as inhibitors of the elongation step in bacterial protein synthesis.…”

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confidence: 99%