35775-20-3

Upstream product

• 51151-95-2 α-L-rhodinoside 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 133578-67-3 Narbosine A 
• 133646-45-4 Narbosine B 
• 27518-97-4 (S)-4,5-Dihydroxy-hexanal 
• 78164-00-8 vineomycin A₁ 

Relevant academic research and scientific papers

Secondary Metabolites by Chemical Screening, 18 - Narbosines, New Carbohydrate Metabolites from Streptomyces

In the culture broth of two new Streptomyces strains several novel 2,3,6-trideoxy-L-threo-hexose (rhodinose) metabolites, narbosines A to E (2-6,8,9), were detected besides α-N-acetylanhydro-L-ornithine (11) by using the chemical screening method.Their structures were deduced from spectroscopical data as well as from chemical transformations.Narbosine A (2/3) was shown to be a 1:1 anomeric mixture of α-L-rhodinopyranosyl-(1->4)-α/β-L-rhodinopyranose, the others are partially oxidatively and reductively transformed derivatives of 2/3 .A destinct antiviral activity was observed for the described metabolites.Key Words: Narbosines / Metabolites, secondary / Streptomyces / Rhodinosides

SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID

L-Glutamic acid has been converted into a separable mixture of D-amicetono- and L-rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide.Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars.In spite of some improvements in the preparation of 2, the optical yield of this step was only ca. 80percent, but one crystallisation from chloroform raised the optical purity to 96percent.The subsequent steps produced a loss in optical purity of only 4percent.