94120-03-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate is used as a key intermediate in the synthesis of lankacidin, which has potential applications in the development of new drugs with diverse biological activities.
Used in Chemical Synthesis:
Methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate can be used as a starting material or building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate can be used as a research tool in the study of the biosynthesis of lankacidin and other related natural products. It can also be used to investigate the structure-activity relationships of these compounds and their potential applications in various fields.

Upstream product

• 106622-90-6 (4S,5S)-4-(2-carbethoxyethenyl)-2,2,4,5-tetramethyl-1,3-dioxolane 
• 2605-68-7 methyl 2-(triphenylphosphoranylidene)propionate 
• 106544-31-4 (4R,5S)-4-(2-carbethoxyethenyl)-2,2,4,5-tetramethyl-1,3-dioxolane 
• 102271-41-0 (2R,3S,4S,5R)-6-Methoxy-2,3-dimethyl-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Blockage of the early step of lankacidin biosynthesis caused a large production of pentamycin, citreodiol and epi-citreodiol in Streptomyces rochei

In our effort to find the key intermediates of lankacidin biosynthesis in Streptomyces rochei, three UV-active compounds were isolated from mutant FS18, a gene disruptant of lkcA encoding a non-ribosomal peptide synthetase (NRPS)-polyketide synthase (PKS) hybrid enzyme. Their structures were elucidated on the basis of spectroscopic data of NMR and MS. Two compounds of a higher mobile spot on silica gel TLC (Rf =0.45 in CHCl3 -MeOH=20:1) were determined to be an epimeric mixture of citreodiol and epi-citreodiol at the C-6 position in the ratio of 2:1. In contrast, the compound of a lower mobile spot (Rf =0 in CHCl3 -MeOH=20:1) was identical to a 28-membered polyene macrolide pentamycin. The yields of citreodiols and pentamycin in FS18 were 5- and 250-fold higher compared with the parent strain. Introduction of a second mutation of srrX, coding a biosynthetic gene of the signaling molecules SRBs, into mutant FS18 did not affect the production of three metabolites. Thus, their production was not regulated by the SRB signaling molecules in contrast to lankacidin or lankamycin.

Isolation and stereostructures of citreoviral, citreodiol, and epicitreodiol

Three new metabolites (citreoviral, citreodiol, and epicitreodiol) have been isolated from the mycelium of Penicillium citreo-viride B. (IFO 6050) and their stereostructures have been elucidated on the basis of their spectral data coupled with some chemical evidence. Furthermore, the absolute configurations of citreodiol and epicitreodiol have been determined by synthesis of the corresponding antipodes starting from L-rhamnose.