56618-58-7Relevant academic research and scientific papers
(3S,8E)-1,3-Dihydroxy-8-decen-5-one, a Metabolite of Streptomyces fimbriatus
Keller-Schierlein, Walter,Wuthier, Damian,Drautz, Hannelore
, p. 1253 - 1261 (1983)
From the cultures of Streptomyces fimbriatus, strain Tue 2335, the title compound 1 was isolated by solvent extraction, chromatography, and distillation.Its constitution was determined by spectroscopic investigations of 1 and some of its derivatives, and the chirality by transformation to (R)-1,3-isopropylidenedioxydecane (12); a reference sample of the latter was prepared from (R)-methyl 3-hydroxydecanoate (10).In the equilibrium mixture the keto form 1 predominates the two hemiacetals 2a and 2b.Compound 1 is inactive against bacteria, yeasts and fungi.
Total Synthesis and Stereochemical Assignment of Sunshinamide and Its Anticancer Activity
Goswami, Rajib Kumar,Mondal, Joyanta,Sarkar, Ruma,Sen, Prosenjit
, (2020/02/15)
Total synthesis of cyclodepsipeptide sunshinamide has been achieved for the first time using a convergent approach. The key features of this synthesis comprise Crimmins acetate aldol, Shiina esterification, amide coupling, macrolactamization, and an Isub
Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies
Hahn, Frank,Ro?, Theresa,Schr?der, Marius,Wunderlich, Johannes
supporting information, (2020/07/04)
Studies on the biosynthetic processing of polyene thioester intermediates are complicated by limited access to appropriate substrate surrogates. We present a step-economic synthetic access to biomimetic β-ketopolyene thioesters that is based on an Ir-catalyzed reductive Horner-Wadsworth-Emmons olefination. New β-ketotriene and pentaenethioates of pantetheine and N-acetylcysteamine were exemplarily synthesized via short and concise routes. The usefulness of these compounds was demonstrated in an in vitro assay with the ketoreductase domain MycKRB from mycolactone biosynthesis.
Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions
Wang, Hongling,Wang, Yuhuang,Chen, Xingkuan,Mou, Chengli,Yu, Shuyan,Chai, Huifang,Jin, Zhichao,Chi, Yonggui Robin
supporting information, p. 7440 - 7444 (2019/10/02)
A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.
Synthesis and Characterization of Four Diastereomers of Monorhamnolipids
Palos Pacheco, Ricardo,Eismin, Ryan J.,Coss, Clifford S.,Wang, Hui,Maier, Raina M.,Polt, Robin,Pemberton, Jeanne E.
, p. 5125 - 5132 (2017/05/04)
Rhamnolipids are amphiphilic glycolipids biosynthesized by bacteria that, due to their low toxicity and biodegradability, are potential replacements for synthetic surfactants. The previously limited access to pure materials at the gram scale has hindered
Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
Lin, Zechao,Li, Jiahong,Huang, Qingfei,Huang, Qiuya,Wang, Qiwei,Tang, Lei,Gong, Deying,Yang, Jun,Zhu, Jin,Deng, Jingen
, p. 4419 - 4429 (2015/05/13)
A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).
Rapid total synthesis of cyclic lipodepsipeptides as a premise to investigate their self-assembly and biological activity
De Vleeschouwer, Matthias,Sinnaeve, Davy,Van Den Begin, Jos,Coenye, Tom,Martins, Jose C.,Madder, Annemieke
supporting information, p. 7766 - 7775 (2014/07/07)
A rapid and efficient total synthesis is reported for the cyclic lipodepsipeptide pseudodesmin A. This member of the Pseudomonas viscosin group is active against Gram-positive bacteria and features self-assembling properties. A conserved serine residue within the lactone macrocycle is exploited for initial immobilization on 2-chlorotrityl chloride resin through ether formation with the side-chain alcohol. Subsequent elongation proceeds through Fmoc solid-phase peptide synthesis, including automated incorporation of the enantioselectively synthesized (R)-3-hydroxydecanoic acid lipid tail. Following esterification to generate the incipient lactone bond, the macrocycle is formed by on-resin head-to-tail macrolactamization and cleaved from the resin to give the desired compound in good purity. The short and efficient synthesis route allows rapid generation of analogues by facile variation of both the peptide and lipid moieties with good control of epimerization while maximizing automation. Synthesis of the pseudodesmin A enantiomer yields identical self-assembly and biological activity to that observed for the natural compound, showing that activity is not mediated by chiral interactions. A D-Asn8 analogue developed en route retains self-assembly, but loses activity. The synthesis strategy should be generally applicable for the rapid generation of analogues from various cyclic lipodepsipeptide groups, allowing an investigation of their self-assembling properties and structure-activity relationships. Accessing cyclic peptides: An efficient, rapid, high-yielding, and versatile total synthesis of the self-assembling Pseudomonas cyclic lipodepsipeptide pseudodesmin A is presented (see figure). The approach involves solid-phase peptide synthesis with serine side-chain immobilization. The route allows rapid analogue production, unlocking structure-activity relationship studies. The self-assembly and biological activity properties of two analogues are reported, including the enantiomer.
Syntheses and studies of amamistatin B analogs reveals that anticancer activity is relatively independent of stereochemistry, ester or amide linkage and select replacement of one of the metal chelating groups
Wu, Chunrui,Miller, Patricia A.,Miller, Marvin J.
supporting information; experimental part, p. 2611 - 2615 (2011/06/20)
A series of analogs of the amamistatin natural products was designed and synthesized to facilitate additional anticancer structure-activity relationships. The results indicate that the anticancer activity is relatively independent of stereochemistry, ester or amide linkage and replacement of the oxazoline/oxazole based iron-binding group with a catechol.
The absolute configurations of hydroxy fatty acids from the royal jelly of honeybees (Apis mellifera)
Kodai, Tetsuya,Nakatani, Takafumi,Noda, Naoki
body text, p. 263 - 270 (2012/02/01)
9-Hydroxy-2E-decenoic acid (9-HDA) is a precursor of the queen-produced substance, 9-oxo-2E-decenoic acid (9-ODA), which has various important functions and roles for caste maintenance in honeybee colonies (Apis mellifera). 9-HDA in royal jelly is considered to be a metabolite of 9-ODA produced by worker bees, and it is fed back to the queen who then transforms it into 9-ODA. Recently we found that 9-HDA is present in royal jelly as a mixture of optical isomers (R:S, 2:1). The finding leads us to suspect that chiral fatty acids in royal jelly are precursors of semiochemicals. Rather than looking for semiochemicals in the mandibular glands of the queen bee, this study involves the search for precursors of pheromones from large quantities of royal jelly. Seven chiral hydroxy fatty acids, 9,10-dihydroxy-2E-decenoic, 4,10-dihydroxy-2E-decenoic, 4,9-dihydroxy-2E-decenoic, 3-hydroxydecanoic, 3,9-dihydroxydecanoic, 3,11-dihydroxydodecanoic, and 3,10-dihydroxydecanoic acids were isolated. The absolute configurations of these acids were determined using the modified Mosher's method, and it was revealed that, similar to 9-HDA, five acids are present in royal jelly as mixtures of optical isomers. AOCS 2010.
Asymmetric synthesis of secondary alcohols from primary alcohols via intramolecular carbenoid C-H insertion catalyzed by rhodium(II) 3-phenylcholestane-2-carboxylate
Hwang, Cheol Hee,Chong, You Hoon,Song, Sue Yeon,Kwak, Hyo Shin,Lee, Eun
, p. 816 - 817 (2007/10/03)
Chiral secondary alcohols may be prepared from primary alcohols via asymmetric C-H insertion reactions of α′-alkoxy-α-diazoketones catalyzed by rhodium(II) (2R,3K)-3-phenylcholestane-2-carboxylate.
