chiral

Nutlin-3a ((−)-Nutlin-3), the active enantiomer of Nutlin-3, inhibits MDM2-p53 interactions and stabilizes the p53 protein.

(S)-2-Hydroxy-3-phenylpropanoic acid (L-(−)-3-Phenyllactic acid) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via lactate dehydrogenase. The D-form is derived from bacterial sources, while the L-form is endogenous. Phenyllactate levels are normally very low in blood or urine, but high levels indicate phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to a deficiency of phenylalanine hydroxylase (PAH), causing phenylalanine to convert to phenylpyruvic acid rather than tyrosine.

Gamibetal (4-Amino-3-hydroxybutyric Acid) is used as a chiral reagent in the synthesis of antiepileptic and hypotensive drug GABOB and analogues. Also used in the preparation of HIV-1 inhibitors derived from Betulinic Acid (B330250).

Inexpensive starting material for chiral synthesis.

4-N-Dodecyloxyphenol (p-Dodecyloxyphenol) is a compound that can be used as an additive to ferroelectric or ferroelectric liquid crystals or to display the SmC phase and has no chiral groups.

D-Lyxose (D-(-)-Lyxose) is used as a chiral building block.

2-Acetylthiazole (2-Acetylthiazole;2 Acetylthiazole) is used in the preparation of chiral alcohols, triazolothiazoles, it is also used in aldol condensation reactions.

Hexylene glycol (Diolane), colorless liquid, is a chiral diol. It is an industrial compound produced from diacetone alcohol by hydrogenation.

L-Hydroxyproline (L-Hydroxyprolin) is one of the hydroxyproline (Hyp) isomers. L-Hydroxyproline is a useful chiral building block in the production of many pharmaceuticals.

Levoglucosan (1,6-anhydro-b-D-Glucose) is an anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It is formed from the pyrolysis of carbohydrates, such as starch and cellulose. Levoglucosan can also be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers. Levoglucosan is also produced via caramelization of sugar. Consumption of caramel or caramel-containing sweets can lead to a short-term 5X increase in urinary levels of levoglucosan (from 20 uM/mM creatinine to 100 uM/mM creatinine).

D-alpha-Methylbenzyl isothiocyanate is an antioxidant. It induces phase II enzyme activity and is also used as a chiral agent.

1,3,3,5,5-pentamethylcyclohexan-1-amine hydrochloride, also known as PAC, is a cyclic amine commonly used as a chiral auxiliary in asymmetric syntheses including the Diels-Alder reaction, hydroxyaldol reaction, and Michael addition.

L-Dithiothreitol (L-Dtt) is a chiral bidentate dithiol with two stereogenic centers. It may be used in chiroptical response research.

Metolachlor is an organic compound. Metolachlor is also widely used as an herbicide.

3-hydroxy-3-phenylpentanamide is a chiral compound belonging to the class of beta-hydroxyamides. In neurology, it has been shown to have neuroprotective effects against ischemic brain injury and cerebral hemorrhage. In psychiatry, it has been studied as a potential treatment for anxiety, depression and addiction. In oncology, it has been shown to have antitumor activity by inducing apoptosis and inhibiting tumor growth.

D-(-)-Lactic acid sodium (Sodium D-lactate) is an organic acid. It is a chiral molecule, consisting of two optical isomers, L-lactic acid and D-lactic acid, with the L-isomer being the most common in living organisms. D-(-)-Lactic acid sodium also is a microbial metabolite.

Cedryl acetate (Cedranyl acetate) , an acetylated from cedarwood oil, has been applied to chemistry for its properties as a chiral and cell signaling reagent with antifungal and immunotoxicity functions.

YK 4-279, an inhibitor of RNA Helicase A (RHA), binds to the oncogenic transciption factor EWS-FLI1.

(-)-CAMPHOR (L-Camphor) also known by its common name as (-)-Camphor is a chiral intermediate of camphor and is used as a flavour additive in foods and sweetners.

L-Hamamelose plays a significant role as a chiral building block in synthesizing a wide variety of enantiopure compounds.

Dibutyl tartrate is an agent of chiral surfactant.

Furalaxyl is an fungicide of acyl amino chiral.

AMG-315 is a Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes. AMG-315 is a chiral arachidonoyl ethanolamide (AEA) analogue or (13S,1′R)-dimethylanandamide. AMG-315 is a high affinity ligand for the CB1 receptor (Ki of 7.8 ± 1.4 nM) that behaves as a potent CB1 agonist in vitro (EC50 = 0.6 ± 0.2 nM). AMG-315 is the first potent AEA analogue with significant stability for all endocannabinoid hydrolyzing enzymes as well as the oxidative enzymes COX-2. AMG-315 will serve as a very useful endocannabinoid probe.

9(S)-HETE is an enantiomer which makes up 50% of (±)9-HETE . There are no reports of 9(S)-HETE occurring as an enzymatic lipoxygenation product. Whereas 12(S)-HETE promotes adhesion of several cell lines to endothelial cell monolayes, 9(S)-HETE and other positional HETEs are without effect. Stereochemical assignment of the (S) enantiomer is based on comparison of chiral HPLC retention times to published results.

Ribulose is an important metabolite in pentose interconversions. Ribulose is useful for analyzing L-ribose isomerase, engineering yeast for xylose metabolism, interesting chiral pool compound.

13(R)-HODE cholesteryl ester was originally extracted from atherosclerotic lesions. It remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. 13(R)-HODE cholesteryl ester can be used as a standard for analysis of chiral HODE cholesteryl esters.

Fluprostenol isopropyl ester, a potent agonist of the F-series prostaglandin receptor, serves as a prodrug utilized clinically as an ocular hypotensive agent for glaucoma treatment. An impurity, 13(R),14(R)-epoxy fluprostenol isopropyl ester, arises during its production, existing as a chiral enantiomer of the epoxide. The pharmacological properties of this specific enantiomer have yet to be thoroughly investigated.

(+)-Fenchol, a monoterpenoid discovered in various plants including Cannabis, serves both as a precursor in synthesizing other terpenoids and as a chiral building block for the organic synthesis of numerous compounds. Additionally, formulations incorporating (+)-fenchol are employed as fragrance ingredients.

(–)-G-lactone, a bicyclic γ-lactone, serves as a chiral synthon for prostaglandin and a building block. It is formed through an asymmetric Baeyer-Villiger oxidation reaction. Additionally, (–)-G-lactone has been utilized in the synthesis of HIV-1 protease inhibitors.

Nb-enantride is a novel chiral trialkylborohydride for the asymmetric reduction of ketones.

RAC 109 is a chiral antiarrhythmic agent.

Arecaidine propargyl ester is an agonist of M2muscarinic acetylcholine receptors (mAChRs).1It selectively binds to M2over M1, M3, M4, and M5mAChRs in CHO cells expressing the human receptors (Kis = 0.0871, 1.23, 0.851, 0.977, and 0.933 μM, respectively). Arecaidine propargyl ester induces contractions in isolated guinea pig atrium (pD2= 8.67). It induces apoptosis and the production of reactive oxygen species (ROS) in U87 and U251 glioblastoma cells when used at a concentration of 100 μM.2Arecaidine propargyl ester decreases mean arterial blood pressure in normotensive cats (ED25= 1.9 nmol/kg).3It is toxic to house flies (Musca) when administered at a dose of 75 μg/fly.4 1.Scapecchi, S., Matucci, R., Bellucci, C., et al.Highly chiral muscarinic ligands: the discovery of (2S,2’R,3’S,5’R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide methyl iodide, a potent, functionally selective, M2 partial agonistJ. Med. Chem.49(6)1925-1931(2006) 2.Di Bari, M., Tombolillo, B., Conte, C., et al.Cytotoxic and genotoxic effects mediated by M2 muscarinic receptor activation in human glioblastoma cellsNeurochem. Int.90261-270(2015) 3.Porsius, A.J., and Van Zwieten, P.A.Central action of some cholinergic drugs (arecaidine esters) and nicotine on blood pressure and heart rate of catsProg. Brain Res.47131-135(1977) 4.Honda, H., Tomizawa, M., and Casida, J.E.Insect muscarinic acetylcholine receptor: Pharmacological and toxicological profiles of antagonists and agonistsJ. Agric. Food Chem.55(6)2276-2281(2007)

9(R)-HETE, which constitutes 50% of (±)9-HETE, activates RXRγ-dependent transcription 1.5-fold relative to a control at a concentration of 300 nM. The stereochemical assignment of the (R) enantiomer is based on the comparison of chiral HPLC retention times to published results.

Prothioconazole (Proline 480 SC Fungicide) is a chiral triazole fungicide in plant pathogen control.

Ethofumesate is a chiral herbicide. Ethofumesate acts by inhibiting mitosis and reducing photosynthesis and plant respiration.

The phospholipases are an extensive family of lipid hydrolases that function in cell signaling, digestion, membrane remodeling, and as venom components. The calcium-independent phospholipases (iPLA2) are a PLA2 subfamily closely associated with the release of arachidonic acid in response to physiologic stimuli. (R)-Bromoenol lactone ((R)-BEL) is an irreversible, chiral, mechanism-based inhibitor of calcium-independent phospholipase γ (iPLA2γ). Unlike (S)-BEL, (R)-BEL does not inhibit iPLA2β except at high doses of 20-30 μM. (R)-BEL inhibits human recombinant iPLA2γ with an IC50 of approximately 0.6 μM.

11(R)-HETE is biosynthesized by 11(R)-LOs of the sea urchin, S. purpuratus, and the fresh water hydra, H. vulgaris. The biological activity of 11(R)-HETE relates to oocyte maturation and tentacle regeneration, respectively, in these two species. 11(R)-HETE is also produced when aspirin-treated recombinant COX-2 is incubated with arachidonic acid. Stereochemical assignment of the (R) enantiomer is based on comparison of chiral HPLC retention times to published results.

Arverapamil is a chiral metabolite of Verapamil.

Acenocoumarol is a short-lived oral anti-coagulant, which, like warfarin, functions by inhibiting vitamin K epoxide reductase. It has higher intrinsic anticoagulant potency than warfarin and phenprocoumon, when evaluated in vitro. Acenocoumarol has a single chiral center that gives rise to two different enantiomeric forms. (S)-Acenocoumarol has a shorter plasma elimination half-life (1.8 hours) and faster plasma clearance (28.5 L/hour), compared to the (R)-enantiomer (6.6 hours, 1.9 L/hour). The S-enantiomer undergoes extensive first-pass metabolism during absorption from the gastrointestinal tract, whereas (R)-acenocoumarol is rapidly absorbed and provides essentially complete oral bioavailability. Perhaps related to these pharmacokinetic characteristics, (S)-acenocoumarol is less potent in vivo as an anti-coagulant than the (R)-enantiomer. As the clearance of acenocoumarol is ~20-fold faster than that for warfarin, the plasma concentrations of acenocoumarol are substantially lower than those for warfarin in patients receiving long-term treatment.

L-alpha-Methylbenzyl isothiocyanate is an antioxidant. It induces phase II enzyme activity and is also used as a chiral agent.

8(S)-HETE, a major lipoxygenase product in PMA-treated murine epidermis, activates mouse keratinocyte protein kinase C with an IC50 of 100 μM and selectively activates PPARα at concentrations as low as 0.3 μM. The stereochemical assignment of the (S) enantiomer is based on comparison of chiral HPLC retention times to published results.

6-O-Sulfo-β-cyclodextrin is a sulfated cyclodextrin.1It has been used for the chiral separation of nadolol racemates by capillary electrophoresis. 1.Wang, F., Dowling, T., Bicker, G., et al.Electrophoretic chiral separation of pharmaceutical compounds with multiple stereogenic centers in charged cyclodextrin mediaJ. Sep. Sci.24(5)378-384(2001)

9(S)-HODE cholesteryl ester, originally extracted from atherosclerotic lesions, has an uncertain origin of its oxidized fatty acid portion, which may result from either enzymatic lipoxygenation or random lipid peroxidation. This compound can be used as a standard for analyzing chiral HODE cholesteryl esters.

Reboxetine (Norebox) is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesylate (i.e. methanesulfonate) salt is sold under trade names including Edronax, Norebox, Prolift, Solvex, Davedax or Vestra. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R, R)-(-)- and (S, S)-(+)-reboxetine.

Corey lactone aldehyde benzoate serves as a versatile, chiral intermediate in the synthesis of prostaglandins and their analogs.

D-arabinose-13C5 is the 13C labeled compound of D-arabinose. D-arabinose has a CAS number of 10323-20-3. Inexpensive starting material for chiral synthesis.

RU 35929 is a chiral antiamnesic agent.

Acetylmandelic acid, (+)- is a chiral derivatizing agent,and used for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.

D-Lysine lactam is a chiral building block.1,2It has been used in the synthesis of a chiral antibiotic synthetic intermediate, as well as in the stereoselective synthesis of neurokinin (NK) receptor antagonists. 1.Kumar, A., Bhashkar, B., Bhavsar, J., et al.Catalytic reduction: Efficient synthesis of chiral key intermediate of besifloxacin hydrochlorideDer Pharma Chemica7(9)297-3000(2015) 2.Gerspacher, M., Lewis, C., Ball, H.A., et al.Stereoselective preparation of N-[(R,R)-(E)-1-(3,4-dichlorobenzyl)-3- (2-oxoazepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide, a potent and orally active dual neurokinin NK(1)/NK(2) receptor antagonistJ. Med. Chem.46(16)3508-3513(2003)

(1S)-CCR2 antagonist 1, a left-handed chiral form of CCR2 antagonist 1, exhibits high affinity and a long residence time as a CCR2 antagonist, with an inhibition constant (K i) of 2.4 nM [1].

D-Ribose(mixture of isomers) (D-(-)-Ribose), commonly referred to as simply ribose, is a five-carbon sugar found in all living cells. Ribose is not an essential nutrient because it can be synthesized by almost every tissue in the body from other substances, such as glucose. It is vital for life as a component of DNA, RNA, ATP, ADP, and AMP.

D-(-)-Arabinose is a reducing sugar useful as a substrate in analysis of arabinose isomerases and synthesis of D-erythroascorbic acid in yeast. It shows strong growth inhibition against the Caenorhabditis elegans with an IC50 of 7.5 mM.

L-(+)-Arabinose selectively inhibits intestinal sucrase in a non-competitive manner, thereby preventing glucose elevation induced by sucrose intake.

Arabinose (DL-Arabinose), also known as (+/-)-arabinose or aloe sugar. Arabinose has been primarily detected in feces. Within the cell, Arabinose is primarily located in the cytoplasm. Arabinose exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, Arabinose can be found in sweet basil and tamarind.