PP 5 - Med chem

Chiral molecule def

molecule is not superimposable on its mirror image

Chiral molecule contain ____

at least 1 asymmetric carbon (4 diff groups)

symmetric plane def

divides a molecule into symmetric halves (at least 1 identical group)

stereoisomers def

compounds have same molecular formula and differ only in stereochemical arrangement of fun groups attached to 1 or more atoms

enantiomers def

1 of 2 stereoisomers that are non-superimposable mirror images of each other

Do symmetric carbons have r/s configurations?

NO

Diastereomers def

same formula differ only in stereochemical arrangement → NOT mirror images

D/L designation based on _____

glyceraldehyde

D/L designation used for _____

amino acid and sugar molecules

D/L designation based on which carbon

2nd from top (first T)

R/S configuration if anything but lowest priority group is on dashed line →

we flip the configuration

Name this molecule

glyceraldehyde

D-glyceraldehyde is r or s?

R

L-glyceraldehyde is r or s?

S

R/S configuration: wedges are ____, dashes are ____

horizontal, vertical

R/S configuration: if H (or lowest priority group) is horizontal _____

flip configuration

R/S configuration: if H (or lowest priority group) is vertical _____

keep configuration

optic rotation designation: (+)

drug molecule rotates plane polarized light to the right

optic rotation designation: (-)

drug molecule rotates plane polarized light to the left

unpolarized light

natural waves vibrate in various planes

polarization

passing unpolarized light thru a polarizing filter allows vibration specific to only a single plane to pass thru

optic rotation designation importance for drug manufacturing

measuring allows us to confirm drugs identity, purity, and enantiomeric composition for quality control (makes sure correct enantiomer was produced of drug for desired therapeutic effect)

optic rotation designation does NOT

determine R or S configuration, it can only confirm

stereochemsitry importance in pharmaceutical chemsitry

enantiomers produce different pharmacological effects bc biological targets are chiral or metabolize differently

drugs bind to desired biological targets in there

active conformations

Z-isomer priority groups on

same side of = (Za same)

E-isomer priority groups on

diff sides of = (EWWW)

conformational isomers def

same molecule with single bond(s) rotations (NOT enantiomers)

active conformation def

the conformation that the drug molecule binds to its desired biological target

chemical basis of drug action ____ & ___

active conformation and drug-target complex

drug target complex (E-I) has ____

lower energy than the drug + free target

Target protein and drug molecule must

both adopt active conformations to bind correctly

active conformations maximize

non-covalent bonds btw drug and target