33796-86-0

Upstream product

• 7367-90-0 ethyl β-hydroxyoctanoate 
• 13283-91-5 3-oxooctanoic acid 
• 66-25-1 hexanal 
• 22348-95-4 methyl 3-oxooctanoate 
• 105-36-2 ethyl bromoacetate 
• 10488-95-6 ethyl 3-oxooctanoate 
• 142-61-0 Hexanoyl chloride 
• 7367-87-5 3-hydroxyoctanoic acid methyl ester 
• 5163-67-7 (E)-oct-3-enoic acid 

Downstream Products

• 66997-64-6 (S)-methyl 3-hydroxyoctanoate 
• 126442-53-3 (S)-3-hydroxyoctanoic acid benzyl ester 
• 7367-87-5 3-hydroxyoctanoic acid methyl ester 
• 541-50-4 2-acetoacetic acid 
• 192883-14-0 N-(3-hydroxyoctanoyl)-L-homoserine lactone 

Relevant academic research and scientific papers

Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound

Provided are: a method for producing an aliphatic carboxylic acid compound safely and easily from a starting material that can be obtained or produced industrially without generating a harmful substance such as haloform; and a pyridine compound adduct of an aliphatic ketone compound. The method for producing an aliphatic carboxylic acid compound is a method for producing an aliphatic carboxylic acid compound represented by Formula (I), and comprises: a first step for obtaining a pyridine compound adduct by adding a pyridine compound to an aliphatic ketone compound having an alpha-methyl groupin the presence of an oxidizing agent; and a second step of hydrolyzing the pyridine compound adduct in the presence of a base. In the Formula, R1 represents a substituted or unsubstituted linear alkyl group having 4-8 carbon atoms or a substituted or unsubstituted branched alkyl group having 4-8 carbon atoms; M represents hydrogen, a metal belonging to Group 1 or Group 2 of the periodic table, amethyl group, an ethyl group, an n-propyl group or an isopropyl group.

Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity

A new cyclic lipopeptide, phototemtide A (1), was isolated from Escherichia coli expressing the biosynthetic gene cluster pttABC from Photorhabdus temperata Meg1. The structure of 1 was elucidated by HR-ESI-MS and NMR experiments. The absolute configurations of amino acids and 3-hydroxyoctanoic acid in 1 were determined by using the advanced Marfey's method and comparison after total synthesis of 1, respectively. Additionally, three new minor derivatives, phototemtides B–D (2–4), were identified by detailed HPLC–MS analysis. Phototemtide A (1) showed weak antiprotozoal activity against Plasmodium falciparum, with an IC50 value of 9.8 μm. The biosynthesis of phototemtides A–D (1–4) was also proposed.

The synthesis of medium-chain-length β-hydroxy esters via the reformatsky reaction

The synthesis of medium-chain-length β-hydroxy esters in good yield via the Reformatsky reaction is described. This work will be used as the basis for further investigation of hydroxyalkanoate polymers as potential feedstock for biofuel production.

Characterization of FabG and FabI of the Streptomyces coelicolor dissociated fatty acid synthase

Streptomyces coelicolor produces fatty acids for both primary metabolism and for biosynthesis of the secondary metabolite undecylprodiginine. The first and last reductive steps during the chain elongation cycle of fatty acid biosynthesis are catalyzed by FabG and FabI. The S. coelicolor genome sequence has one fabI gene (SCO1814) and three likely fabG genes (SCO1815, SCO1345, and SCO1846). We report the expression, purification, and characterization of the corresponding gene products. Kinetic analyses revealed that all three FabGs and FabI are capable of utilizing both straight and branched-chain β-ketoacyl-NAC and enoyl-NAC substrates, respectively. Furthermore, only SCO1345 differentiates between ACPs from both biosynthetic pathways. The data presented provide the first experimental evidence that SCO1815, SCO1346, and SCO1814 have the catalytic capability to process intermediates in both fatty acid and undecylprodiginine biosynthesis.

Graphiumins, new thiodiketopiperazines from the marine-derived fungus Graphium sp. OPMF00224

Eight new thiodiketopiperazines, designated as graphiumins A to H (1-8), were isolated along with bisdethiobis(methylthio)-deacetylaranotin (9) and bisdethiobis(methylthio)-deacetylapoaranotin (10) from the culture broth of the marine-derived fungus Graph

Total synthesis and structural validation of cyclodepsipeptides solonamide A and B

Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chemical synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereo-selective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochemistry of the auxiliary in the aldol steps we gained access to the natural products as well as their β3-epimers.

Catalytic asymmetric hydroboration of β,γ-unsaturated Weinreb amides: Striking influence of the borane

Subtle differences in the structure of the borane strongly influence the catalytic efficiency and level of enantioselectivity in the catalytic asymmetric hydroboration of β,γ-unsaturated Weinreb amides.

Formation of an enolate intermediate is required for the reaction catalyzed by 3-hydroxyacyl-CoA dehydrogenase

Fluorinated substrate analogs were synthesized and incubated with rat liver 3-hydroxyacyl-CoA dehydrogenase, which reveals that the formation of an enolate intermediate is required for the reaction catalyzed by the enzyme.

Enantioselective reduction of β-keto acids with engineered streptomyces coelicolor

Compelling evidence for the intermediacy of the free β-keto acid 1, rather than the corresponding enzyme-bound thiolate as previously proposed, in the biosynthesis of the antibiotic actinorhodin (2) was obtained from studies of the enantioselective reduction of a range of β-keto acids by the engineered strain of S. coelicolor CH999/pIJ5675. This excellent whole-cell biotransformation system gave the desired S β-hydroxy acids with >95% ee.

PHA E and PHA C components of poly(hydroxy fatty acid) synthase from thiocapsa pfennigii

PCT No. PCT/DE95/01279 Sec. 371 Date Jul. 3, 1997 Sec. 102(e) Date Jul. 3, 1997 PCT Filed Sep. 15, 1995 PCT Pub. No. WO96/08566 PCT Pub. Date Mar. 21, 1996The present invention relates to a process for the production of poly (hydroxy fatty acids) as well as recombinant bacterial strains for carrying out the process. In addition, new poly(hydroxy fatty acids) and new substrates for the production of conventional and new poly(hydroxy fatty acids) are described. Moreover, the invention also relates to a DNA fragment, which codes for a PhaE and a PhaC component of the poly(hydroxy fatty acid) synthase from Thiocapsa pfennigii, as well as the corresponding poly (hydroxy fatty acid) synthase protein.