Structure of neooxazolomycin, an antitumor antibiotic

Takahashi, Kanji; Kawabata, Michihiro; Uemura, Daisuke; Iwadare, Shuichi; Mitomo, Ryuji; Nakano, Fumio; Matsuzaki, A

doi:10.1016/s0040-4039(00)98516-2

Cited by 69 publications

(52 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(2). The NMRspectra of 1 were similar to those of oxazolomycin except for the appearance of a doublet methyl (<5 1.69/17.9) and a quartet oxymethine (3 4.82/78.4) instead of an oxymethylene in 2, thus indicating that one hydrogen of the oxymethylene in 2 was displaced with the methyl as was the case with curromycin B (3).…”

mentioning

confidence: 71%

16-Methyloxazolomycin, a New Antimicrobial and Cytotoxic Substance Produced by a Streptomyces sp.

1997

View full text Add to dashboard Cite

Triene antibiotics containing /Mactone-y-lactam bicyclospiro and oxazole rings are unique metabolites produced by Streptomyces spp., such as oxazolomycins1'2) and curromycins.3'4)In the course of our continuing search for novel antimicrobial agents from microorganisms, an actinomycete strain Streptomyces sp. isolated from a soil sample collected in Taejon, Korea, was found to produce a new antibacterial 16-methyloxazolomycin (1). In this paper, we describe the production, isolation, structural elucidation and biological activities of 1. The strain was cultured in the seed mediumconsisting of glucose 2%, starch 1%, soybean flour 2.5%, yeast extract 0.4%, NaCl 0.2%, K2HPO4 0.005% and beef extract 0.1% (adjusted to pH 7.3 before sterilization).The seed culture was carried out on a rotary shaker (250rpm) at 28°C for 24 hours in 500-ml Erlenmeyer flasks containing 100ml of the seed medium. Then, the seed culture (100ml) was inoculated to a 50-liter jar fermenter containing 10 liters of the production medium (antifoam 0.08%). Fermentation was carried out at 27°C for 4 days with aeration (10 liters/minute) under constant agitation (250 rpm).The isolation of 16-methyloxazolomycin was guided by the use of Bacillus subtilis IAM1069 as a test organism. The culture broth was centrifuged to separate the mycelial cake. The mycelial cake was stirred overnight in 70% aqueous acetone (5 liters) and filtered. The filtrate was concentrated in vacuo to remove the organic solvent, DEC. 1997 resulting in an aqueous solution.

show abstract

mentioning

confidence: 71%

16-Methyloxazolomycin, a New Antimicrobial and Cytotoxic Substance Produced by a Streptomyces sp.

1997

View full text Add to dashboard Cite

show abstract

“…Finally, the synthesis of salinosporamide (73) was achieved from 95 in a six-step sequence involving the removal of the p-methoxybenzyl group, reductive opening of the cyclic acetal, (Me 2 AlTeMe) 2 -promoted dealkylative cleavage 101) of the methyl ester, β-lactonization, and chlorination. 82,84) Oxazolomycin A and neooxazolomycin, originally isolated from a strain of Streptomyces by the group of Uemura in 1985, 102,103) constitute a family of structurally unique oxazole polyene lactam-lactone antibiotics together with seven other congeners identified to date (Chart 21). These oxazolomycins exhibit wide-ranging, potent inhibitory activity against Gram-positive bacteria and antiviral activity against vaccinia, herpes simplex type I, and influenza A (WSN; H1N1) as well as in vivo (74) had long been the only achievement until we have recently reported the syntheses of neooxazolomycin (74) 82) and oxazolomycin A (75).…”

Section: Total Synthesis Of Salinosporamide Amentioning

confidence: 99%

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Hatakeyama

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Total syntheses of structurally and biologically intriguing natural products relying on new synthetic methodologies are described. This article features cinchona alkaloid-catalyzed asymmetric Morita-BaylisHillman reactions, heterocycle syntheses based on rhodium-catalyzed C-H amination and indium-catalyzed Conia-ene reactions, and their utilization for the syntheses of the phoslactomycin family of antibiotics, glutamate receptor agonists and antagonists, and alkaloids with characteristic highly substituted pyrrolidinone core structures.

show abstract

“…strain KBFP-2025 (Mori, 1985;Takahashi, 1985) and later rediscovered in the fermentation broth of Streptomyces albus strain JA3453. (Gräfe, 1992) Their molecules characterized by a densely functionalized -lactam/-lactone spirocycle, which is linked through a short polyketide fragment, two polyenic tethers and an amide bond to the unsubstiuted oxazole ring.…”

Section: Virginiamycin Mmentioning

confidence: 99%

Total synthesis of antibiotics: recent achievements, limitations, and perspectives

Prusov

2013

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

show abstract

Structure of neooxazolomycin, an antitumor antibiotic

Cited by 69 publications

References 0 publications

16-Methyloxazolomycin, a New Antimicrobial and Cytotoxic Substance Produced by a Streptomyces sp.

16-Methyloxazolomycin, a New Antimicrobial and Cytotoxic Substance Produced by a Streptomyces sp.

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Total synthesis of antibiotics: recent achievements, limitations, and perspectives

Contact Info

Product

Resources

About