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Atom which is the focus of stereoisomerism in a molecule
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least
Stereocenter
Molecules which are non-mirror image, non-identical stereoisomers
(related) stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers
Diastereomer
Geometric property of some molecules and ions
stereogenic element is a stereogenic center, or stereocenter. In the case of organic compounds, stereocenters most frequently take the form of a carbon atom
Chirality_(chemistry)
Chemical compound
3-aminopropanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter. In terms of its biosynthesis, it is formed by the degradation of dihydrouracil
Β-Alanine
Naming convention for stereoisomers of molecules
purpose of the CIP system is to assign an R or S descriptor to each stereocenter and an E or Z descriptor to each double bond so that the configuration
Cahn–Ingold–Prelog priority rules
Cahn–Ingold–Prelog_priority_rules
Chemical reaction
two reactants have carbonyls adjacent to a pre-existing stereocenter, then the new stereocenters may form at a fixed orientation relative to the old. This
Aldol_reaction
Type of chirality
Most commonly, a stereocenter with 2 identical substituents differing only in having opposite chirality are bonded to the same stereocenter. For example,
Pseudochirality
Stereoisomers that are nonsuperposable mirror images of each other
a type of stereocenter. A chirality center is also called a chiral center or an asymmetric center. Some sources use the terms stereocenter, stereogenic
Enantiomer
Comprehensive list of compounds structurally related to fentanyl
Second asterisks are placed by potential stereocenters as indicators (*). Third the pairs of each stereocenters R and S orientations are combined through
List_of_fentanyl_analogues
Chemical compound
Computed Properties Hydrogen Bond Donor Count 0 Defined Atom Stereocenter Count 7 Undefined Atom Stereocenter Count 1 Rotatable Bond Count 5
Cholestene
Hydrocarbon compound with the formula C8H18
constitutional isomers. 8 of these isomers have one stereocenter; 3 of them have two stereocenters. Achiral isomers: 2-Methylheptane 4-Methylheptane 3-Ethylhexane
Octane
Alkaloid chemical compound
share a framework isomerism. The aporphine alkaloids usually have a stereocenter. The (R)-configured glaucine can be synthesized from (S)-glaucine. Aporphine
Aporphine_alkaloids
When molecules have the same atoms and bond structure but differ in 3D orientation
the same, then there is no stereoisomer and the double bond is not a stereocenter, e.g. propene, CH3CH=CH2 where the two substituents at one end are both
Stereoisomerism
Chemical compound
from its closely related peptidase inhibitor phosphoramidon by a single stereocenter. Kitagishi, Keiko; Hiromi, Keitaro (1984). "Inhibitory spectrum of talopeptin
Talopeptin
Optically inactive isomer in a set of stereoisomers
are optically active. This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is superposable on its
Meso_compound
Chemical compound
characterized by a spiro[5.5]undecane core with an all-carbon quaternary stereocenter at the junction of the spirocycle. Sigma-Aldrich Co., (−)-β-Chamigrene
Chamigrene
Subdiscipline of chemistry
simplified standard ways of representing the 3D positioning of atoms around a stereocenter. One common convention uses a bond drawn as a solid wedge to indicate
Stereochemistry
Chemical compound
All the double bonds are cis and the absolute configuration of the stereocenter is (S). Ectocarpene was isolated from algae Ectocarpus (order Ectocarpales)
Ectocarpene
Chemical compound
octane. Its structural formula is CH3CH2CH(CH3)CH2CH2CH2CH3. It has one stereocenter. Its refractive index is 1.398 (20 °C, D).[citation needed] "3-METHYLHEPTANE
3-Methylheptane
Fluxional process in trigonal-pyramidal molecules
transition state. For a compound that would otherwise be chiral due to a stereocenter, pyramidal inversion allows its enantiomers to racemize. The general
Pyramidal_inversion
Psychedelic drug
with no acute tolerance observed. LSD is a chiral compound with two stereocenters at the carbon atoms C-5 and C-8, so that theoretically four different
LSD
Organic reaction between a silyl enol ether and an aldehyde or formate
Simplified overview with a stereocenter
Mukaiyama_aldol_addition
Chemical compound
ruthenium catalyst and a chiral bisphosphine ligand sets the second stereocenter. The carboxylate is esterified by reaction with thionyl chloride to form
Sacubitril
Chemical compound family
2-pentanol, and 3-methyl-2-butanol (methyl isopropyl carbinol), contain stereocenters, and are therefore chiral and optically active. The most important amyl
Amyl_alcohol
Antioxidant compounds with vitamin E activity
stereocenters. In the image of RRR-α-tocopherol below, all three stereocenters are in the R form. However, if the middle of the three stereocenters were
Tocopherol
Central nervous system stimulant
transdermal patches. Methylphenidate is a chiral compound with two stereocenters; clinical use overwhelmingly utilizes the racemate threo diastereomer
Methylphenidate
Form of stereoisomerism in carbohydrates
the absolute configuration of the anomeric carbon and the most distant stereocenter from the anomeric carbon are the same (SS or RR giving the α configuration)
Anomer
Nonsteroidal anti-inflammatory drug
derivatives such as ketoprofen, flurbiprofen and naproxen, contains a stereocenter in the α-position of the propionate moiety. The product sold in pharmacies
Ibuprofen
Sterol biosynthesized by all animal cells
paints. Cholesterol has 256 stereoisomers that arise from its eight stereocenters. Only two of the stereoisomers have biochemical significance: nat-cholesterol
Cholesterol
Stereoisomerism due to hindered rotation
Sa, in analogy to the traditional R/S for a traditional tetrahedral stereocenter. Axially chiral biaryl compounds are prepared by coupling reactions,
Atropisomer
8 Å2 Formal Charge 1 Complexity 530 Covalently Bonded Unit Count 1 Compound is Canocalized Yes Isotope Atom Count 0 Defined Atom Stereocenter Count 0
Avicine
Dipolar compound
regioselective, and have the potential to form four new contiguous stereocenters. Azomethine ylides thus have high utility in total synthesis, and formation
Azomethine_ylide
Chemical agent and drug construction
chiral molecule containing four stereocenters within the quinuclidine bicyclic amine group. With four stereocenters present in the structure, 16 possible
Quinine_total_synthesis
group to the newly formed enone group. The reaction step creates two stereocenters leading to two diastereomeric pairs of enantiomers. By the nature of
Galantamine_total_synthesis
Chemical compound
ricinoleic, etc. This compound has the R configuration at the alcohol-bearing stereocenter, and it is of the Z configuration at the olefin. Lesquerolic acid is
Lesquerolic_acid
Organic compound with a C=C–OH group
then it is prochiral, forming a new stereocenter when in keto form. Conversely, enolization racemizes that stereocenter.[citation needed] Usually the tautomerization
Enol
Poisonous substance used as pesticide
the strychnine molecular structure, with its specific array of rings, stereocenters, and nitrogen functional groups, is a complex synthetic target, and
Strychnine
Chemical compound
of vancosamine (top) and epivancosamine (bottom). Note the differing stereocenter at carbon 4. Names IUPAC name (3S,4S,5S)-3-Amino-4,5-dihydroxy-3-methylhexanal
Vancosamine
Rotation of the plane of linearly polarized light as it travels through a chiral material
specific chiral stereocenter with the molecule, rather than a property of the molecule as a whole. A molecule having exactly one chiral stereocenter (usually
Optical_rotation
Chemical group (–C4H9) derived from butane
Butan-2-yl (sec-butyl) group is chiral. The carbon atom at position 2 is a stereocenter. It has four different groups attached: −H, −CH3, −CH2−CH3, and −R (the
Butyl_group
Asymmetric catalyst derived from proline
chiral compound, is readily and cheaply available. It transfers its stereocenter to the catalyst which in turn is able to drive an organic reaction selectively
CBS_catalyst
Preferential formation of one chiral isomer over another in a chemical reaction
state, the β-stereocenter is oriented anti- to the incoming nucleophile, as seen in the Felkin–Anh model. The polar X group at the β-stereocenter is placed
Asymmetric_induction
Pairs of molecules with same chemical formula showing different spatial orientations
unspecified stereochemistry or a mixture of isomers (as with tetrahedral stereocenters). A crossed double-bond has been used sometimes; it is no longer considered
Cis–trans_isomerism
Antihypotensive medication
metabolite desglymidodrine ranges from -0.01 to 0.15. Midodrine contains a stereocenter and consists of two enantiomers, making it a racemate; i.e., a 1:1 mixture
Midodrine
Medication mainly used to treat gout
grams per mole. Colchicine has one stereocenter located at carbon 7. The natural configuration of this stereocenter is S. The molecule also contains one
Colchicine
Chemical compound
analogs include diphenhydramine, and doxylamine. Pheniramine contains a stereocenter and can exists as either of two enantiomers. The pharmaceutical drug
Pheniramine
Chemical compound
Hyperforin is a unique PPAP because it consists of a C8 quaternary stereocenter which was a synthetic challenge unlike other PPAP synthetic targets.
Hyperforin
Type of antibiotic
five-membered. Neomycin C are stereoisomers of each other and differ by only one stereocenter (C-5‴), one giving the R conformation and the other giving the S conformation
Neomycin
Representation method in chemistry
unspecified stereochemistry or a mixture of isomers (as with tetrahedral stereocenters). A crossed double-bond has been used sometimes; it is no longer considered
Skeletal_formula
Cholesterol-lowering medication
purity in the final drug substance, and hence establishing the first stereocenter became a key aspect of the overall design. The final commercial production
Atorvastatin
SSRI antidepressant
better choice for the elderly or comorbid patients. Citalopram has one stereocenter, to which a 4-fluoro phenyl group and an N, N-dimethyl-3-aminopropyl
Citalopram
Preference of an electrocyclic reaction towards inward or outward rotation of substituents
operate include chiral Lewis acid catalysts, induction via neighboring stereocenters (in which case the torquoselectivity is a case of diastereoselectivity)
Torquoselectivity
Anti-arrhythmic medication
for use in the United States in November 1989. Propafenone contains a stereocenter and consists of two enantiomers. This is a racemate, a 1:1 mixture of
Propafenone
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
stereochemistry of nine stereocenters. Cytovaricin, synthesized by D. A. Evans in 1990. Blue and red bonds indicate stereocenters set with the use of chiral
Chiral_auxiliary
Covalent bond joining a sugar molecule to another group
bonds by the relative stereochemistry of the anomeric position and the stereocenter furthest from C1 in the saccharide. Pharmacologists often join substances
Glycosidic_bond
Chemical compound
product with H₂ over Pd/C leads to terbutaline. Terbutaline contains a stereocenter and consists of two enantiomers. This is a racemate, ie a 1:1 mixture
Terbutaline
Chemical compound
Connecticut. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two enantiomers with quite different potency, the (R)-enantiomer
AM-1220
Chemical compound
differences in chirality and therefore the ability to obtain desired stereocenters in a molecule is of great importance to the pharmaceutical industry
Jacobsen's_catalyst
Chemical compound
reaching the olfactory receptors to some extent. Picaridin contains two stereocenters: one where the hydroxyethyl chain attaches to the ring, and one where
Picaridin
Chemical notation for the handedness of a chiral molecule or group
oxide gives (−)-glyceric acid (2), a reaction that does not alter the stereocenter. Thus the absolute configuration of (−)-glyceric acid must be the same
Absolute_configuration
Ability of a chemical reaction mechanism to differentiate between stereoisomers
(for the interconversion of existing stereocenters) and stereoselective ones (for the creation of new stereocenters), where also the optical activity of
Stereospecificity
Chemical compound
launched, being the last rocket fueled with Syntin. Syntin has two stereocenters at the central cyclopropane ring. Thus, four stereoisomers exist: In
Syntin
Monosaccharide sugar
cyclic form can exist as two anomers, named alpha and beta, since a new stereocenter is generated upon cyclization at the site of the carbonyl. In the pyranose
Galactose
Prefix in organic chemistry nomenclature
for every amino acid except for glycine. Therefore, the α-carbon is a stereocenter for every amino acid except glycine. Glycine also does not have a β-carbon
Locant
Medication for overactive bladder
suggest that it is eliminated through the liver. Oxybutynin contains one stereocenter. Commercial formulations are sold as the racemate. The (R)-enantiomer
Oxybutynin
Chemical compound
introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (−)-3a-hydroxyfuroindoline as a building block, construction of
Neoxaline
Chemical compound found in oil of lemon eucalyptus
p-menthane. A total of eight stereoisomers are possible, based on the three stereocenters of the ring. Depending on the source, one or more may predominate. PMD
P-Menthane-3,8-diol
Chemical compound
from its closely related peptidase inhibitor talopeptin by a single stereocenter. Because of its enzyme inhibitory properties, phosphoramidon is widely
Phosphoramidon
Chemical production of a pharmaceutical drug
coli. Control of stereochemistry is important: the molecule has three stereocenters and the sought-after isomer is only 1 of 8 stereoisomers.[citation needed]
Oseltamivir_total_synthesis
Beta blocker medication
main physicochemical properties of metoprolol. Metoprolol contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1:1 mixture
Metoprolol
Chemical compound
morphine depending on what assay is used. Like prodine, it has two stereocenters and four possible enantiomers, but the activity of these has not been
LS-115509
Chemical compounds with the same molecular formula but different atomic arrangements
Electromerism Isomerization Isomery (botany) Ligand isomerism Nuclear isomer Stereocenter Structural isomerism Tautomer Vitamer Petrucci, Ralph H.; Harwood, William
Isomer
Medication and insecticide
has four stereoisomers (two enantiomeric pairs), arising from the two stereocenters in the cyclopropane ring. The trans enantiomeric pair is known as transpermethrin
Permethrin
Antihypertensive drug of the calcium channel blocker class
Lethargy Sinus tachycardia Transient hypotension Isradipine contains a stereocenter and consists of two enantiomers, more precisely atropisomers. This is
Isradipine
Chemical compounds and groups containing nitrogen with a lone pair (:N)
C-C distances. The energy barrier for the nitrogen inversion of the stereocenter is about 7 kcal/mol for a trialkylamine. The interconversion has been
Amine
Notation in organic chemistry for double bonds
unspecified stereochemistry or a mixture of isomers (as with tetrahedral stereocenters). A crossed double-bond has been used sometimes; it is no longer considered
E–Z_notation
represents a powerful strategy to build molecular complexity with up to two stereocenters in a single operation. Generally, there are four categories of reaction
Alkene_carboamination
Ability of a chemical reaction to produce an unequal mixture of stereoisomers
mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one.
Stereoselectivity
Chemical compound
medicine for induction in surgical anaesthesia. Thiobutabarbital contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1:1 mixture
Thiobutabarbital
Chemical compound
norleucine, having two hydrogen atoms less. The α-carbon atom is not a stereocenter. Cycloleucine is a non-metabolisable amino acid that specifically and
Cycloleucine
Chemical compound
as the 7-O-glucoside of noricaritin. Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible. It
Phellamurin
Nucleophilic addition of an allyl, allenyl or propargyl-stannane
efficient methods for the production of contiguous, oxygen-containing stereocenters in organic molecules. Since many naturally-occurring polymers contain
Organostannane_addition
Chemical compound
from plants such as Siberian larch and milk thistle. Taxifolin has two stereocenters on the C-ring, as opposed to quercetin which has none. For example,
Taxifolin
catalyze stereospecific reduction of polyketides. Inversion of an alcohol stereocenter to the opposite stereoisomer is possible via replacement of a wild-type
Erythronolide_synthase
Chemical compound
name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(−)-DOB is the eutomer. This is an important finding as it is suggestive
2,5-Dimethoxy-4-bromoamphetamine
2,5-Dimethoxy-4-bromoamphetamine
Change in optical rotation of a chiral substance due to interconversion of anomers
two constituent anomers (i.e. the interconversion of their respective stereocenters) until equilibrium is reached. Cyclic sugars show mutarotation as α
Mutarotation
General anaesthetic
halide (not an ether like many other anesthetics). The structure has one stereocenter, so (R)- and (S)-optical isomers occur.[citation needed] The commercial
Halothane
Group of stereoisomers
1997). The chirality of the second stereocenters is determined by the configuration of the existing stereocenter alpha to the ketone derived from either
Hydroxybupropion
Antifungal medication
Trichophyton mentagrophytes Trichophyton rubrum Sertaconazole contains a stereocenter and consists of two enantiomers. The pharmaceutical drug is a racemate
Sertaconazole
Chemical compound
are diastereomeric pentitols, differing in the configuration of two stereocenters. Arabitol was initially produced, soon after its discovery, through
Arabitol
Chemical reaction
lactone can be formed while maintaining other stereocenters. The ring closure can even be driven by stereocenters adjacent to the carbon-carbon multiple bond
Iodolactonization
Pericyclic chemical reaction
retention of both the 1,3-dipole and the dipolarophile. When two or more stereocenters are generated during the reaction, diastereomeric transition states
1,3-Dipolar_cycloaddition
Group of drugs used against malaria
stereoselective hydroboration/oxidation to establish the "off-ring" methyl stereocenter on the propene side chain; two sequential lithium-reagent mediated alkylations
Artemisinin
Antihypertensive medication
concentration is reached after approximately 90 minutes. Alfuzosin contains a stereocenter, so is chiral, with two enantiomeric forms, (R)- and (S)-alfuzosin. The
Alfuzosin
Chemical compound
L-alliin, differing in the orientation of the oxygen atom on the sulfur stereocenter. A newer route, reported by Koch and Keusgen in 1998, allows stereospecific
Alliin
Naming system for building blocks of carbohydrate
denote the relative configuration of the anomeric carbon to that of the stereocenter at the other end of the carbon chain. If the conformation (R or S) is
Monosaccharide_nomenclature
Chemical compound
dizziness and disorientation. sec-Butyl acetate is chiral. It has one stereocenter, carbon 2 in the sec-butyl group. The names of the two enantiomers are:
Sec-Butyl_acetate
Chemical compound
N-bromosuccinimide to trigger an oxidative rearrangement, forming the quaternary stereocenter in a diastereoselective manner. Fuji spirotryprostatin B synthesis In
Spirotryprostatin_B
Chemical reaction
carbon-carbon bonds, and the potential for introduction of up to four new stereocenters in one step. [4+4] reactions are forbidden in the ground state and often
4+4_Photocycloaddition
Chemical reaction
High diastereoselectivity is usually observed, and the newly formed stereocenter usually share the same configuration with the starting amino acid. This
Petasis_reaction
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