Med Chem Exam #1

Alanine

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Hydrophobic interactions
*Not best amino acid to use

Valine

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Hydrophobic interactions

Leucine

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Hydrophobic interactions

Isoleucine

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Hydrophobic interactions
Van der Waals

Phenylalanine

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Stacking
Hydrophobic interactions

Serine

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Dipole-dipole
Hydrogen bonding
Ion-dipole

Threonine

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Dipole-dipole
Hydrogen bonding
Ion-dipole

Cysteine

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Dipole-dipole
Hydrogen bonding (acceptor only)
Ion-dipole

Tyrosine

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Dipole-dipole
Hydrogen bonding
Ion-dipole
Stacking

Methionine

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Dipole-dipole
Hydrogen bonding
Ion-dipole
Hydrophobic interactions

ω oxidation

Alkanes (3 or more C)
Cycloalkanes (monosubstituted, even-numbered)

Affects last carbon in chain
*Makes primary alcohols in alkanes
*Makes secondary alcohols in cycloalkanes in para position

ω-1 oxidation

Alkanes (3 or more C)
Cycloalkanes (monosubstituted, even-numbered)

Affects second to last carbon in chain
Oxygen is inserted between C and H
*Secondary alcohols made in both alkanes and cycloalkanes (ortho)

Peroxidation and Epoxidation

*Rule: At least one H atom on each alkene C atom

Peroxidation:
Alkenes are transformed (two O atoms are added)

Epoxidation:
Peroxide collapses and only one O atom remains (cyclic ether with three ring atoms)

Allylic Oxidation

*Allylic position is the C atom directly attached to the alkene (aliphatic and not part of aromatic hydrocarbon)

*Allylic C must have at least one H atom attached

Transformed into an alcohol

Aromatic Hydroxylation

Aromatic hydrocarbons undergo para hydroxylation and are transformed into a phenol

Phenols undergo ortho hydroxylation and are transformed into a catechol (ortho to OH group)

*Ipso carbon: C to which R group is attached

*Meta hydroxylation NEVER occurs

Benzylic Oxidation

Benzylic position is the C directly attached to an aromatic ring

C must be aliphatic, not part of an aromatic ring, have one or more H atoms attached, and cannot have a heteroatom already attached (OH, NR2)

Creates an alcohol

Alcohol Oxidation

Primary and secondary alcohols only

*Rule: C bearing the OH group must have one or more H atoms attached

Primary alcohol transforms into aldehyde and then carboxylic acid

Secondary alcohol transforms into ketone

Oxidative O-dealkylation

*Rule: C that bears the ether O atom has one or more H atoms attached

Ether transformed to give an alcohol and either an aldehyde or a ketone

S-dealkylation

*Rule: C that bears the thioether S atom has one or more H atoms attached

Thioethers

Aliphatic Alkanes and Cycloalkanes

Hydrophobic
Neutral
Contributes to Absorption
Bulky
Hydrophobic Interactions*

*Aliphatic alkanes with 3 or more carbons and no branching can also participate in van der Waals interactions

Alkenes and Cycloalkenes

Hydrophobic
Neutral
Contributes to Absorption
Bulky
Hydrophobic Interactions

Alkynes

Hydrophobic
Neutral
Contributes to Absorption
Linear
Hydrophobic Interactions

Aromatic Hydrocarbons

Hydrophobic
Neutral
Contributes to Absorption
Flat
Stacking/Hydrophobic Interactions

Halogenated Hydrocarbons

Halogens (F, Cl, Br, I)

Hydrophobic*
Neutral
Contributes to Absorption*
Character (shape) depends on hydrocarbon
Function (interaction) depends on hydrocarbon

*F has hydrophilic character and contributes to solubility

Alcohols

Primary, secondary, and tertiary (R-OH where R is not an aromatic ring)

Hydrophobic (R), Hyrophilic (OH)
Neutral
Contributes to Absorption (R), Contributes to Solubility (OH)
Dipole-dipole, H-bonding (A+D), Ion-dipole (as dipole)

Thiols

R-SH where R is not an aromatic ring

Hydrophobic (R), Hyrophilic (SH)
Acidic
Contributes to Absorption (R), Contributes to Solubility (SH)
Dipole-dipole, H-bonding (D), Ion-dipole (as dipole)

Phenols

Ar-OH

Hydrophobic (R=Ar), Hyrophilic (OH)
Acidic; pKa ~ 10
Contributes to Absorption (R=Ar), Contributes to Solubility (OH)
Dipole-dipole, H-bonding (A+D), Ion-dipole (as dipole)

Thiophenols

Ar-SH

Hydrophobic (R=Ar), Hyrophilic (SH)
Acidic; pKa ~ 6.6
Contributes to Absorption (R=Ar), Contributes to Solubility (SH)
Dipole-dipole, H-bonding (D), Ion-dipole (as dipole)

Ethers

R-O-R (2 non-carbonyl atoms)

Hydrophobic (R), Hyrophilic (O)
Neutral
Contributes to Absorption (R), Contributes to Solubility (O)
Dipole-dipole, H-bonding (A), Ion-dipole (as dipole)

Thioethers

R-S-R (2 non-carbonyl C atoms)

Hydrophobic
Neutral
Contributes to Absorption
Hydrophobic interactions

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