lesson 1 midterm chirality Flashcards
have the same molecular formula but different structural
Isomers
have the same molecular formula and the same connectivity of atoms, but differ in the spatial arrangement
stereoisomers
Nonsuperposable mirror images are
enantiomers
Objects that are not superposable on
their mirror images are
chiral
chiral (from
the Greek: ____).
cheir, hand
A carbon with four different groups
bonded to it is called a _
stereocenter
f an object and its mirror image are
superposable, they are identical and
there is no possibility of enantiomerism
achiral
note:kapag may stereocentr auto chiral na yun
note:kapag may stereocentr auto chiral na yun
Objects that are nonsuperposable on their mirror images are ___ (they show handedness)
chiral
Objects that are superposable on their mirror images are ___ (without chirality)
achiral
is a way to distinguish between
enantiomers without having to draw them and
point to one or the other
R,S system
the
maximum number of possible stereoisomers
is
2n
stereoisomers that are not
mirror images
diastereomers
light waves vibrating in all
planes perpendicular to its direction of
propagation.
Ordinary light
light waves
vibrating only in parallel planes.
Plane-polarized light
an instrument for measuring
the ability of a compound to rotate the
plane of plane-polarized light.
Polarimeter
showing that a
compound rotates the plane of plane-
polarized light.
Optically active
clockwise rotation of the
plane of plane-polarized light
Dextrorotatory
counterclockwise rotation of
the plane of plane-polarized light.
Levorotatory
the observed rotation of an
optically active substance at a concentration of 1 g/mL in a sample tube 10 cm long.
Specific rotation
Chymotrypsin has 251 stereocenters.
Chymotrypsin
The maximum number of stereoisomers possible
is
2251
for a molecule with
one stereocenter, ____(one pair of
enantiomers) are possible.
21 = 2 stereoisomers
two stereocenters, a
maximum of ___(two pair of
enantiomers) are possible.
22 = 4 stereoisomers
three stereocenters, a
maximum of ___(four pairs of
enantiomers) are possible
23 = 8 stereoisomers
To see the relationship between the original and
its mirror image,
rotate the mirror image by 120°
The____applies equally well to molecules with
three or more stereocenters.
2n rule
These are two molecules that are mirror images but
cannot be perfectly stacked on top of each
other
Enantiomers
have a stereocenter and are not
superimposable on their mirror images
Chiral molecules
have no stereocenter and are
superimposable (identical to their mirror images).
Achiral molecules
___ is active as a pain
and fever reliever, while its )____ is
inactive.
(S)-ibuprofen, R enantiomer
Clockwise = R, Counterclockwise = S.
Clockwise = R, Counterclockwise = S.
means “handedness
Chirality
Iodine (I) = 53 → Highest priority (1)
Bromine (Br) = 35 → Second priority (2)
Chlorine (Cl) = 17 → Third priority (3)
Hydrogen (H) = 1 → Lowest priority (4)
Iodine (I) = 53 → Highest priority (1)
Bromine (Br) = 35 → Second priority (2)
Chlorine (Cl) = 17 → Third priority (3)
Hydrogen (H) = 1 → Lowest priority (4)
highly chiral and only work with specific enantiomers
enzyme
S-ibuprofen works as a painkiller.
R-ibuprofen does not work.
S-naproxen is a pain reliever,
but R-naproxen is toxic to the liver!
S-ibuprofen works as a painkiller.
R-ibuprofen does not work.
S-naproxen is a pain reliever,
but R-naproxen is toxic to the liver!
plays a crucial role in dentistry,
particularly in the effectiveness of drugs,
biomaterials, and flavoring agents
Chirality
Many anesthetics used in dentistry, such as
bupivacaine, lidocaine, and artcicaine, exist as chiral
molecules.
Local Anesthetics (Pain Management)
Many antibiotics used in dentistry, like amoxicillin,
have chiral centers.
The correct enantiomer is more effective in fighting
bacterial infections in the mouth
Antibiotics for Oral Infections
Menthol, used in toothpaste and mouthwash, has
two enantiomers
(−)-Menthol gives the cool, minty sensation.
(+)-Menthol has a different scent and does not feel
as refreshing.
Chiral molecules are used in dental implants, resins,
and adhesives to improve biocompatibility.
Biocompatible Dental Materials
a chiral polymer, is used in
some bioresorbable dental materials to aid in
healing.
Polylactic acid (PLA),
is the active form that reduces pain and
swelling in the gums after dental surgery.
S-Ibuprofen
Certain pain relievers and anti-inflammatory drugs
(like ibuprofen) have chiral versions
Enantiomer-Specific Drug Interactions
which
help numb the mouth during procedures like tooth
extractions, root canals, and fillings.
local anesthetics
is a powerful local anesthetic
Bupivacaine
More toxic to the heart and
nervous system.
R-Bupivacaine
Less toxic
and still effective for pain relief.
S-Bupivacaine
it
provides long-lasting numbness with fewer side
effects.
3.
S-Bupivacaine
another chiral anesthetic widely used in
dentistry.
Articaine
is more effective and breaks
down faster in the body, reducing side effects.
S-enantiomer
If the priority order of groups is read in a
clockwise direction, what is the configuration?
r
