Hydrolysis

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What are cyclic nucleotides & what are they used for?

-intracellular second messengers that play a key role in many physiological processes -they are targets for rational design of family-selective inhibitors as therapeutics to treat those biological disorders

Name the insecticide inhibitors of acetylcholinesterase. 3

-paraoxon -parathion -fensulforthion

Pharmacologic activity of a compound is dependent on what 2 things?

-the rate/affinity by the compound reacts/associates with a receptor or active site of an enzyme (sigma) -lipophilic character of the compound (pi)

How many leaving groups are there in hydrolysis of amides?

1 leaving group

What is the most active anti-cocaine catalytic antibody?

12A10

How many leaving groups are there in carbamate hydrolysis?

2

How many leaving groups are there in carbonate hydrolysis?

2 leaving groups

What happens in direct reaction with a water molecule?

OH attaches to carbonyl carbon & H attaches to OR

What is the second bridging site in the active site of both PDE4 & PDE5?

OH1

What metabolizes cAMP & cGMP?

PDE superfamily

What does PDE does viagra also target that causes side effects?

PDE6

What leads to OP poisoning?

aging

What are PDE5 target drugs now being used to treat?

alzheimer's disease

State the order of the 4 compound stability in water.

amide> carbamate> carbonate> ester>

What 2 drugs target PDE4?

antidepressants & memory enhancers

PDE2 drugs have a promising target for.... 2

anxiolytic drugs & memory enhancers

Name an ex of a carboxylic acid drug.

benzocaine, cocaine

Where is the bond broken in hydrolysis of carbonate?

between the carbonyl carbon & both attached oxygens

Where is the bond broken in hydrolysis of amide?

between the carbonyl carbon & the N group

Where is the bond broken in carbamate hydrolysis?

between the carbonyl carbon & the O & the N

Where is the bond broken in carboxylic acid hydrolysis?

between the carbonyl carbon & the attached oxygen

Where is the bond broken in hydrolysis of phosphate esters?

between the oxygen & the R group

For pH>4, which hydrolysis pathway for cAMP is the most important?

cAMP + OH-

What is the dominant hydrolysis pathway in neutral solution?

catalyzed HO-

The mechanism for the hydrolysis of carbonate should be similar to that of-----

ester

State the hydrolysis rate of the 4 types of hydrolysis.

ester> carbonate> carbamate> amide

T/F: p value is independent of the type of reaction in consideration

false every reaction has it's own p value & can be positive or negative

What is the structure of the nerve agent inhibitors of acetylcholinesterase?

fluorinated phosphates

What has to happen to (-) cocaine before it can be hydrolyzed by BChE?

has to go through rotation

larger pi value= higher/lower pharmacologic activity

higher

What is the process of general base-catalyzed hydrolysis?

hydroxide ion attaches to water which attaches to carbonyl

What is the process of specific base-catalyzed hydrolysis?

hydroxide ion can directly attach to a carbonyl

What drugs target PDE5?

male ED drugs (sildenafil, vardenafil, tadalafil)

How does the catabolic Ab catalyze the hydrolysis of cocaine?

more favorably stabilizing the trasition state during the hydrolysis process

Larger pKa than reference= negative/positive sigma value= substituent is electron donating/withdrawing

negative, donating

hydrolysis of phosphate esters X1=OH, X2=OH. How many times can it hydrolyze?

one time

What is used to treat OP poisoning?

oximes like obidoxime & pralidoxime

For very low pH, which hydrolysis pathway for cAMP is the most important?

pH dependent cAMP + H2O

For pH 2-3, which hydrolysis pathway for cAMP is the most important?

pH independent cAMP + H2O

smaller pKa than reference= negative/positive sigma value= substituent is electron donating/withdrawing

positive, withdrawing

Can BChE catalyze hydrolysis of OP compounds?

possibly, yes chemically be depends on wether the OP compounds fits the BChE active site

Name an example in the body of amide hydrolysis.

protein metabolism

What is the process of general acid-catalyzed hydrolysis?

proton attacks water which attacks the carbonyl

What is the process of specific acid-catalyzed hydrolysis?

proton directly attacks carbonyl

What is a hydrolysis reaction?

reaction in which water reacts with a compound to produce other compounds

What are oximes?

recombinant form of human BChE

Name the 2 factors that affect the sigma parameter.

resonance & inducted effects of the functional group

What happens during a hydrolysis reaction?

splits one chemical bond & the addition of the proton and the hydroxide anion form the water

hydrolysis of phosphate esters X1=OR, X2=OR. How many times can it hydrolyze?

three times

T/F: sigma value is independent of the type of reaction in consideration

true

hydrolysis of phosphate esters X1=OH, X2=OR. How many times can it hydrolyze?

two times

Which form of cocaine is natural & biologically active?

(-) cocaine

OP---> phosphorylates the ........ or ..... --->either ...... or ......

-AChE or BChE -either aging or reactivation

Name the nerve agent inhibitors of acetylcholinesterase. 3

-DFP -sarin -soman

Name an example of some drugs that undergo amide hydrolysis.

-Pen G -Lidocaine

Name the 3 ways that cAMP is hydrolyzed.

-cAMP + OH- -cAMP + H2O pH independent -cAMP + H2O pH dependent

Name the 4 hydrolysis pathways.

-direct reaction with water molecule -base-catalyzed hydrolysis -acid-catalyzed hydrolysis -enzymatic hydrolysis

The hydrolysis of carbamate is similar to the hydrolysis of ---- and -----.

-esters -amides


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