96856-99-4

Upstream product

• 3391-86-4 1-octen-3-ol 

Downstream Products

• 124615-23-2 Benzoic acid (1R,2S)-6-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-1-ethyl-2-hydroxy-hex-4-ynyl ester 
• 124615-23-2 Benzoic acid (1S,2R)-6-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-1-ethyl-2-hydroxy-hex-4-ynyl ester 
• 96895-74-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-(S)-1-oxiranyl-hexyl ester 
• 96895-73-7 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-(S)-1-oxiranyl-hexyl ester 
• 1390618-97-9 (S)-2-((R)-1-((4-methoxybenzyl)oxy)hexyl)oxirane 

Relevant academic research and scientific papers

The first stereoselective total synthesis of the Z-isomer of cytospolide e

A convergent and highly stereoselective total synthesis of the Z-isomer of cytospolide E has been achieved via Evan's aldol reaction, Sharpless kinetic resolution and RCM cyclisation.

Metabolism of deuterated erythro-dihydroxy fatty acids in Saccharomyces cerevisiae: Enantioselective formation and characterization of hydroxylactones

Epoxides of fatty acids are hydrolyzed by epoxide hydrolases (EHs) into dihydroxy fatty acids which are of particular interest in the mammalian leukotriene pathway. In the present report, the analysis of the configuration of dihydroxy fatty acids via their respective hydroxylactones is described. In addition, the biotransformation of (±)-erythro-7,8- and -3,4-dihydroxy fatty acids in the yeast Saccharomyces cerevisiae was characterized by GC/EI-MS analysis. Biotransformation of chemically synthesized (±)-erythro-7,8- dihydroxy(7,8-2H2)tetradecanoic acid ((±)-erythro- 1) in the yeast S. cerevisiae resulted in the formation of 5,6-dihydroxy(5,6- 2H2)dodecanoic acid (6), which was lactonized into (5S,6R)-6-hydroxy(5,6-2H2)dodecano-5-lactone ((5S,6R)-4) with 86% ee and into erythro-5-hydroxy(5,6-2H2)dodecano-6- lactone (erythro-8). Additionally, the α-ketols 7-hydroxy-8-oxo(7- 2H1)tetradecanoic acid (9a) and 8-hydroxy-7-oxo(8- 2H1)tetradecanoic acid (9b) were detected as intermediates. Further metabolism of 6 led to 3,4-dihydroxy(3,4- 2H2)decanoic acid (2) which was lactonized into 3-hydroxy(3,4-2H2)decano-4-lactone (5) with (3R,4S)-5=88% ee. Chemical synthesis and incubation of (±)-erythro-3,4-dihydroxy(3,4- 2H2)decanoic acid ((±)-erythro-2) in yeast led to (3S,4R)-5 with 10% ee. No decano-4-lactone was formed from the precursors 1 or 2 by yeast. The enantiomers (3S,4R)- and (3R,4S)-3,4-dihydroxy(3- 2H1)nonanoic acid ((3S,4R)- and (3R,4S)-3) were chemically synthesized and comparably degraded by yeast without formation of nonano-4-lactone. The major products of the transformation of (3S,4R)- and (3R,4S)-3 were (3S,4R)- and (3R,4S)-3-hydroxy(3-2H 1)nonano-4-lactones ((3S,4R)- and (3R,4S)-7), respectively. The enantiomers of the hydroxylactones 4, 5, and 7 were chemically synthesized and their GC-elution sequence on Lipodex E chiral phase was determined.

Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-Hydroxynonenal

trans-4-Hydroxynonenal (HNE) is a major peroxidation product of ω-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N2-γ-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 °C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.