Category: 617-55-0

Liljeblad, Arto; Kanerva, Liisa T. published the artcile< Enzymatic methods for the preparation of enantiopure malic and aspartic acid derivatives in organic solvents>, Synthetic Route of 617-55-0, the main research area is kinetic resolution malic aspartic acid lipase.

The kinetic resolution of malic and aspartic acid diesters as well as of N-butanoylaspartic acid di-Me ester by highly regioselective lipases and acylase I enzymes were studied. Candida antarctica lipase A on Celite catalyzed the enantioselective acylation of the hydroxyl and amino groups. Acylase I from Aspergillus melleus and Candida antarctica lipase B catalyzed the enantioselective alcoholysis of the ester groups at the α- and β-positions, resp.

Tetrahedron: Asymmetry published new progress about Kinetic resolution. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Synthetic Route of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Lagemann, Annika; Dunkel, Andreas; Hofmann, Thomas published the artcile< Activity-Guided Discovery of (S)-Malic Acid 1'-O-β-Gentiobioside as an Angiotensin I-Converting Enzyme Inhibitor in Lettuce (Lactuca sativa)>, Formula: C6H10O5, the main research area is Lactuca malic acid gentiobioside natural antihypertensive ACE inhibitor.

Angiotensin-converting enzyme (ACE), playing a crucial role in the renin angiotensin aldosterone system, is well-known to catalyze the conversion of the decapeptide angiotensin I into the physiol. active octapeptide angiotensin II, triggering blood pressure increasing mechanisms. To meet the demand for natural phytochems. as antihypertensive agents in functional food development, extracts prepared from a series of vegetables were screened for their ACE-inhibitory activity by means of a LC-MS/MS-based in vitro assay. By far the highest ACE inhibition was found for a lettuce extract, in which the most active compound was located by means of activity-guided fractionation. LC-MS, NMR spectroscopy, and hydrolysis experiments followed by ion chromatog. led to the unequivocal identification of the ACE inhibitor as the previously not reported (S)-malic acid 1′-O-β-gentiobioside. This glycoside represents a novel class of ACE-inhibiting phytochems. with a low IC50 value of 27.8 μM. First incubation experiments in saliva and aqueous hydrochloric acid demonstrated the stability of (S)-malic acid 1′-O-β-gentiobioside against salivary glycosidases and stomach acid.

Journal of Agricultural and Food Chemistry published new progress about Angiotensin-converting enzyme inhibitors. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Yamada, S.; Nakayama, K.; Takayama, H. published the artcile< Stereoselective synthesis of (23R,25S)- and (23S,25R)-25-hydroxyvitamin D3 26,23-lactone: determination of the configuration of a metabolite of vitamin D3, calcidiol lactone>, Formula: C6H10O5, the main research area is calcidol lactone stereoselective synthesis; hydroxyvitamin D3 lactone preparation configuration; vitamin D3 hydroxy lactone.

The title diastereoisomeric vitamin D3 lactones I were prepared via the condensation of aldehyde II and dioxolanylethyl sulfone III. (23S,25R)-I was identical with the natural metabolite calcidol lactone.

Proceedings of the Workshop on Vitamin D published new progress about 9,10-Secosteroids Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Booth, Paul M.; Fox, Christina M. J.; Ley, Steven V. published the artcile< Regiospecific alkylation of β-keto thio esters and use in the synthesis of acyltetronic acids>, Synthetic Route of 617-55-0, the main research area is carolic acid; carlosic acid; acetothioacetate alkylation; carbonyl acetothioacetate.

Anions of Me3CSCOCH2COMe react with alkyl halides and carbonyl compounds in a regiospecific manner to afford products which are versatile synthetic intermediates as exemplified by short syntheses of the mold metabolites carolic acid (I) and carlosic acid (II).

Tetrahedron Letters published new progress about Alkylation. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Synthetic Route of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Rotzoll, Nina; Dunkel, Andreas; Hofmann, Thomas published the artcile< Activity-Guided Identification of (S)-Malic Acid 1-O-D-Glucopyranoside (Morelid) and γ-Aminobutyric Acid as Contributors to Umami Taste and Mouth-Drying Oral Sensation of Morel Mushrooms (Morchella deliciosa Fr.)>, COA of Formula: C6H10O5, the main research area is morelid malate glycoside umami morel mushroom Morchella GABA.

Taste activity-guided fractionation of an aqueous morel extract by means of the recently developed taste dilution anal. (TDA) enabled the localization of several umami-like-tasting fractions as well as a fraction imparting an intense mouth-drying sensation to the oral cavity. Hydrophilic interaction liquid chromatog. (HILIC), LC-MS, and amino acid anal. led to the successful identification of γ-aminobutyric acid as the chem. inducer of the mouth-drying and mouth-coating oral sensations imparted by the morel extract Besides the well-known umami-like taste contributors L-glutamic acid, L-aspartic acid, and succinic acid, an addnl. HILIC fraction was isolated and evaluated as tasting umami-like. LC-MS and NMR studies revealed that this fraction consisted of a mixture of (S)-malic acid 1-O-α-D-glucopyranoside and (S)-malic acid 1-O-β-D-glucopyranoside, the structure of which could be successfully confirmed by independent synthesis. To the best of our knowledge, this morel-derived glycoside, named (S)-morelid, has previously not been reported in any food products. Sensory anal. of aqueous solutions of the compounds identified revealed threshold concentrations of 0.02 mmol/L for the mouth-drying effect of γ-aminobutyric acid and 6.0 mmol/L for the umami-like, slightly sour taste of (S)-morelid.

Journal of Agricultural and Food Chemistry published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Polonski, Tadeusz published the artcile< Chiroptical properties and molecular geometry of substituted succinic anhydrides and imides>, Computed Properties of 617-55-0, the main research area is CD succinic anhydride succinimide conformation; mol mechanic succinic anhydride succinimide; UV spectra succinic anhydride succinimide; solvent effect CD anhydride imide.

UV and CD spectra have been measured for several α-substituted succinic anhydrides and imides. The Cotton effect signs corresponding to the two n-π* electronic transitions can be explained with the octant rule. The strong substituent and solvent dependence of the spectra is a result of the equilibrium between two skewed conformers of the five-membered ring. The geometry and relative energies of the conformers were found from mol. mechanics (MM2) calculations

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Circular dichroism. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Computed Properties of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Cicchi, Stefano; Crea, Saverio; Goti, Andrea; Brandi, Alberto published the artcile< Synthesis of new enantiopure γ-amino alcohols: their use as catalysts in the alkylation of benzaldehyde by diethylzinc>, SDS of cas: 617-55-0, the main research area is amino alc asym synthesis; dipolar cycloaddition cyclic nitrone malic acid.

The straightforward synthesis of new enantiopure γ-amino alcs. through 1,3-dipolar cycloaddition to a chiral cyclic nitrone derived from L-malic acid was described. Results of the application of these compounds as chiral catalysts in the alkylation of benzaldehyde with diethylzinc were also reported. The addition of styrene to (S)-4-(1,1-dimethylethoxy)-3,4-dihydro-2H-pyrrole 1-oxide (I), gave predominantly the adduct II which upon subsequent methylation yielded III. In the presence of III as catalyst, the addition of diethylzinc to benzaldehyde gave (R)-α-ethylbenzenemethanol in 54% enantiomeric excess.

Tetrahedron: Asymmetry published new progress about Addition reaction, stereoselective. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, SDS of cas: 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Tararov, Vitali I.; Koenig, Gerd; Boerner, Armin published the artcile< Synthesis of statins. I. Synthesis and highly stereoselective hydrogenation of the statin precursor ethyl (5S)-5,6-isopropylidenedioxy-3-oxohexanoate>, Category: esters-buliding-blocks, the main research area is statin intermediate isopropylidenedioxyoxohexanoate preparation stereoselective hydrogenation.

A search for the large-scale preparation of (5S)-5,6-(isopropylidenedioxy)-3-oxohexanoate, a key intermediate in the synthesis of pharmacol. important statins, starting from (S)-malic acid is described. The synthesis of the required intermediate Me (3S)-3,4-(isopropylidenedioxy)butanoate (I) by Moriwake’s reduction of di-Me (S)-malate has been improved. Direct 2-C chain elongation of ester I using the lithium enolate of tert-Bu acetate has been shown to be successful at a 3- to 5-fold excess of the enolate. Unfortunately, the product, tert-Bu (5S)-5,6-(isopropylidenedioxy)-3-oxohexanoate is unstable during distillation Et (5S)-5,6-(isopropylidenedioxy)-3-oxohexanoate (II) was prepared alternatively on a multigram scale from (3S)-3,4-(isopropylidenedioxy)butanoic acid by activation with N,N’-carbonyldiimidazole and subsequent reaction with Mg(O2CCH2CO2Et)2. A convenient pathway for the in situ preparation of the latter is also described. II can be advantageously purified by distillation The stereochem. of the catalytic hydrogenation of II to Et (5S)-5,6-(isopropylidenedioxy)-3-hydrohyhexanoate (III) has been studied using a number of homogeneous achiral and chiral Rh(I) and Ru(II) complexes with phosphine ligands. A comparison of Rh(I) and Ru(II) catalysts with (S)- and (R)-BINAP as chiral ligands revealed opposite activity in dependence on the polarity of the solvent. No influence of the chiral backbone of substrate II on the enantioselectivity was noted. A ratio of syn/anti-III = 2.3 was observed with an achiral (Ph3P)3RuCl2 catalyst. Ru[(R)-Tol-BINAP]Cl2 neutralized with one equivalent of AcONa afforded the most efficient catalytic system for the production of optically pure syn-III at a preparative substrate/catalyst ratio of 1000:1.

Advanced Synthesis & Catalysis published new progress about Hydrogenation catalysts, stereoselective. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Category: esters-buliding-blocks.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Chinta, Satya P.; Goller, Stephan; Lux, Julia; Funke, Sebastian; Uhl, Gabriele; Schulz, Stefan published the artcile< The Sex Pheromone of the Wasp Spider Argiope bruennichi>, Application In Synthesis of 617-55-0, the main research area is trimethyl methylcitrate sex pheromone spider; methylcitrate diastereomer stereoselective enantioselective preparation identification pheromone wasp spider; argiope bruennichi sex pheromone identification methylcitrate diastereomer.

We investigated the pheromone system of the very characteristic wasp spider Argiope bruennichi, which lives on meadows in the Mediterranean but occurs now also in the temperate zone of middle Europe. Headspace sampling of odors emitted by individual female spiders was performed with activated charcoal traps using glass chambers containing the spiders in 3 developmental stages (subadult, virgin, and mated). The sex pheromone of the wasp spider was identified as a mixture of the 2R,3S- and 2S,3S- isomers of tri-Me methylcitrate. This pheromone is able to attract male spiders in the field in a concentration-dependent manner. Another female-specific spider compound, 3-octanoyloxy-γ-butyrolactone, was identified, but its function remains to be established.

Angewandte Chemie, International Edition published new progress about Argiope bruennichi. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application In Synthesis of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Gao, Jing; Wang, Jian; Wang, Dandan; Pan, Li; Cheng, Maosheng published the artcile< Synthesis of tert-butyl (3R,5S)-6-oxo-3,5-O-isopropylidene-3,5-dihydroxyhexanoate>, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate, the main research area is rosuvastatin intermediate synthesis.

The title compound [i.e., 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronic acid 1,1-dimethylethyl ester] was synthesized from L-(-)-malic acid by esterification, reduction, hydroxy protection, condensation, carbonyl group reduction, hydroxyl protection, deprotection and Swern oxidation with an overall yield of 25%. The title compound is a key intermediate of rosuvastatin.

Zhongguo Yiyao Gongye Zazhi published new progress about Condensation reaction. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics