1852-04-6Relevant articles and documents
Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid
Jang, Hyun-Young,Singha, Kaushik,Kim, Hwan-Hee,Kwon, Yong-Uk,Park, Jin-Byung
, p. 1089 - 1095 (2016)
A practical chemoenzymatic synthetic method for 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid (12-hydroxyoleic acid) was investigated. Biotransformation of ricinoleic acid into the ester (3) via 12-ketooleic acid (2) was driven by recombinant Escherichia coli cells expressing an alcohol dehydrogenase from Micrococcus luteus and the Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440. The carbon-carbon double bond of the ester (3) was chemically reduced, and the ester bond was hydrolyzed to afford n-heptanoic acid (5) and 11-hydroxyundecanoic acid (7), which were converted into other related derivatives. For example, 11-hydroxyundecanoic acid was transformed into 1,11-undecanedioic acid (8) under fairly mild reaction conditions. Whole-cell biotransformation at high cell density (i.e., 20 g dry cells per L) allowed the final ester product concentration and volumetric productivity to reach 53 mM and 6.6 mM h-1, respectively. The overall molar yield of 1,11-undecanedioic acid from ricinoleic acid was 55% based on the biotransformation and chemical transformation conversion yields of 84% and 65%, respectively.
Facile synthesis of gold icosahedra in an aqueous solution by reacting HAuCl4 with N-vinyl pyrrolidone
Yavuz, Mustafa S.,Li, Weiyang,Xia, Younan
, p. 13181 - 13187 (2009)
Herein we describe a protocol that generates Au icosahedra in high yields by simply mixing aqueous solutions of HAuCl4 and N-vinyl pyrrolidone. Our mechanistic study reveals that water plays an important role in this synthesis: as a nucleophile
Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp.
Gabriel, Adeyemi Francis,Li, Zhen,Kusuda, Ryouhei,Tanaka, Chiaki,Miyamoto, Tomofumi
, p. 469 - 475 (2015/09/07)
Six new polyacetylenic alcohols, termed strongylotriols A and B; pellynols J, K, and L; and isopellynol A, together with three known polyacetylenic alcohols, pellynols A, B, and C were isolated from the marine sponges Petrosia sp., and Halichondria sp. collected in Okinawa, Japan. Their planer structures were determined based on 2D-NMR and mass spectrometric analysis of the degraded products by RuCl3 oxidation. The absolute stereochemistry of isolates was examined by their Mosher's esters. The strongylotriols were found to be optically pure compounds, whereas the pellynols are diastereomeric mixtures at the C-6 position. Proliferation experiments using the HeLa and K562 cell lines suggested that the essential structural units for activity are the "hexa-2,4-diyn-1,6-diol" and "pent-1-en-4-yn-3-ol" on the termini.
Divergent process for C10, C11 and C12 ω-amino acid and α,ω-dicarboxylic acid monomers of polyamides from castor oil as a renewable resource
Koh, Moo-Hyun,Kim, Hyeonjeong,Shin, Nara,Kim, Hyun Su,Yoo, Dongwon,Kim, Young Gyu
, p. 1873 - 1878 (2012/08/07)
Polyamides have great potentials for diverse applications and the present production of their monomers mostly relies on resources from fossil fuel. Starting from undecylenic acid, a natural resource, we have developed both divergent and efficient processes for C10, C11 and C 12 ω-amino acid and α,ω-dicarboxylic acid monomers of the polyamides.