Oganomycin A a new cephamycin-type antibiotic produced by Streptomyces oganonensis and its derivatives, oganomycins B, GA and GB.

Gushima, Hiroshi; Watanabe, Shun‐ichi; Saito, Takeshi; Sasaki, Tomohiro; Eiki, Hideo; Oka, Yoshihiko; Osono, Takashi

doi:10.7164/antibiotics.34.1507

Cited by 5 publications

(4 citation statements)

References 6 publications

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“…695 7a-Methoxycephems with cinnamoyl-side chains at C-3 0 were isolated from Streptomyces spp. 320,345,696,697 The cephabacins are produced by some Gram-negative bacteria e.g. Flavobacterium sp.…”

Section: D-(l-a-aminoadipoyl)-l-cysteinyl-d-valine Synthetase (Acvs)mentioning

confidence: 99%

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The enzymes of β-lactam biosynthesis

et al. 2013

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The β-lactam antibiotics and related β-lactamase inhibitors are amongst the most important small molecules in clinical use. Most, but not all, β-lactams including penicillins, cephalosporins, and clavulanic acid are produced via fermentation or via modification of fermented intermediates, with important exceptions being the carbapenems and aztreonam. The desire for more efficient routes to existing antibiotics and for access to new and synthetically challenging ones stimulates continued interest in β-lactam biosynthesis. We review knowledge of the pathways leading to β-lactam antibiotics focusing on the mechanisms, structures and biocatalytic applications of the enzymes involved.

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Section: D-(l-a-aminoadipoyl)-l-cysteinyl-d-valine Synthetase (Acvs)mentioning

confidence: 99%

“…The production of oganomycins can be stimulated by the addition of p-coumaric acid to S. oganonensis cultures. 345 To our knowledge, there have been no studies on the enzymology of this modication nor on the enzymology of the formylamino moiety at C-7 of some cephabacins 115 (Fig. 8).…”

Section: Introduction Of the 7a-methoxy And Formamido-groupsmentioning

confidence: 98%

The enzymes of β-lactam biosynthesis

et al. 2013

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“…Borohydride reduction gave the lactone (177) which could be converted to the substituted amino acid (178). Cyclisation to the ~-lactam gave predominantly the cissubstituted product which was converted to (174) and (172). Conversion to optically active carpetimycin A (173) then followed the procedure of the previous scheme.…”

Section: H (114)mentioning

confidence: 99%

“…Subsequent conversion to (172) was followed by introduction of the (E)-acetamidoethenylthio-substituent, oxidation and deprotection to form (± )-carpetimycin A (173) (134). The second approach (135) was also by way of (172), which in this case was derived from the chiral acid (174). Initially chirality was introduced into the synthetic sequence by enzymic hydrolysis of the prochiral ester (175) giving (176).…”

Section: H (114)mentioning

confidence: 99%