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
Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
supporting information, p. 20394 - 20398 (2020/09/21)
A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.
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.
Microbial synthesis of medium-chain α,ω-dicarboxylic acids and ω-aminocarboxylic acids from renewable long-chain fatty acids
Song, Ji-Won,Lee, Jung-Hoo,Bornscheuer, Uwe T.,Park, Jin-Byung
, p. 1782 - 1788 (2014/06/09)
Biotransformation of long-chain fatty acids into medium-chain α,ω-dicarboxylic acids or ω-aminocarboxylic acids could be achieved with biocatalysts. This study presents the production of α,ω-dicarboxylic acids (e.g., C9, C11, C 12, C13) and ω-aminocarboxylic acids (e.g., C 11, C12, C13) directly from fatty acids (e.g., oleic acid, ricinoleic acid, lesquerolic acid) using recombinant Escherichia coli-based biocatalysts. ω-Hydroxycarboxylic acids, which were produced from oxidative cleavage of fatty acids via enzymatic reactions involving a fatty acid double bond hydratase, an alcohol dehydrogenase, a Baeyer-Villiger monooxygenase and an esterase, were then oxidized to α,ω- dicarboxylic acids by alcohol dehydrogenase (ADH, AlkJ) from Pseudomonas putida GPo1 or converted into ω-aminocarboxylic acids by a serial combination of ADH from P. putida GPo1 and an ω-transaminase of Silicibacter pomeroyi. The double bonds present in the fatty acids such as ricinoleic acid and lesquerolic acid were reduced by E. coli-native enzymes during the biotransformations. This study demonstrates that the industrially relevant building blocks (C9 to C13 saturated α,ω- dicarboxylic acids and ω-aminocarboxylic acids) can be produced from renewable fatty acids using biocatalysis.
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.
(-)-Duryne and its homologues, cytotoxic acetylenes from a marine sponge Petrosia sp.
Hitora, Yuki,Takada, Kentaro,Okada, Shigeru,Ise, Yuji,Matsunaga, Shigeki
experimental part, p. 1262 - 1267 (2011/07/30)
Six linear acetylenes, (-)-duryne (1) and (-)-durynes B-F (2-6), were isolated from the marine sponge Petrosia sp. Their structures were elucidated by NMR and tandem FABMS analyses. The positions of the olefinic bonds were confirmed by ozonolysis experiments, and the absolute configurations were determined by the modified Mosher's method. Compound 1 was found to be the enantiomer of duryne, a previously reported sponge metabolite. Compounds 1-6 show cytotoxicity against HeLa cells with IC50 values between 0.08 and 0.50 μM. (Chemical Equation Presented).
METHOD FOR THE SYNTHESIS OF DIACIDS OR DIESTERS FROM NATURAL FATTY ACIDS AND/OR ESTERS
-
Page/Page column 6, (2010/12/29)
The invention relates to a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x—COOR, in which n is an integer between 5 and 14, R is either H or an alkyl radical of 1 to 4 carbon atoms, from natural long-chain monounsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule of the general formula CH3—(CH2)n—CHR1—CH2—CH═CH—(CH2)p—COOR, in which R is H or an alkyl radical with 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are equal or different and are indices between 2 and 11. The method comprises: during a first step, converting the natural fatty acid or ester by pyrolysis or by ethenolysis, into a ω-monounsaturated fatty acid or ester of the general formula CH2═CH—(CH2)m—COOR, in which m is equal to p or p+1, depending on the nature of the processed fatty acid/ester and the conversion used; during a second step, submitting the product thus obtained to a metathesis or homometathesis reaction for obtaining a compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)m—COOR, or cross-metathesis with a compound of formula R2OOC—(CH2)r—CH═CH—R3, in which R2 is either H or an alkyl radical front with 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R3 is H, CH3 or COOR2, thus defining a cyclic or molecule or not, in order to obtain an unsaturated compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)r—COOR2, and during a third step, converting the unsaturated compound into a saturated compound by hydrogenation of the double bond.
Isolation and characterization of aliphatic constituents of Tephrosia purpurea
Bhatnagar,Kapoor
, p. 973 - 974 (2007/10/03)
n-Hentriacontanol has been isolated from pod husk as well as seeds whereas trans-2-tridecene-1,13-dioic acid, a new compound isolated from pod husk of Tephrosia purpurea. The compounds have been characterized on the basis of spectral data analysis and chemical reactions.
A new, modulated, oxidative ring cleavage of α-nitrocycloalkanones by Oxone: Synthesis of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters
Ballini, Roberto,Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio
, p. 1049 - 1050 (2007/10/03)
By the appropriate choice of the reaction conditions Oxone produces the ring cleavage of α-nitrocycloalkanones affording good yields of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters, respectively, regardless the ring size and/or the presence of an alkyl group as substituent.
