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Organic chemistry > Thiols > Flashcards

Thiols Flashcards

1
Q

Characteristics?

A 
Sulfhydryl group
Liquids
Reducing agents
Slightly soluble --> no H bonds with water
Lower Thiols --> Toxic 
More acidic than alcohols
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2
Q

CH3Ch2-SH

A

Ethylmercaptan

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3
Q

CH3SH

A

Methylmercaptan

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4
Q

Name “Mercaptan”?

A

Mercaptan reaction with Mercuric salts

Affinity for Mercury

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5
Q

Toxicity of Heavy metals?

A

Blocking SH in the active sides of some enzymes

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6
Q

Oxidation products (Strong/Mild) ?

A

Mild: Alkyl Disulfides
Strong: Sulfinic / Sulfonic acid

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7
Q

Linking of a Polypeptide chain?

A

2 Residues of CystEine build Disulfide bonds –> CystIne residue as a Linkage
–> Resistant to Denaturation

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8
Q

Important Derivatives?

A 
Mustard gas
Dimercaprol
Gluthathione 
Cysteamine
Taurine
Lipoid acid 
Allyl Disulfide
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9
Q

Mustard gas

A

Warfare agents

World war 1 –> Heavy oil liquid

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10
Q

Mustard gas medicine

A

Burns
Blindness
Death

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11
Q

Dimercaprol

A

British anti Lewisit

Antidote to Lewisite

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12
Q

Lewisite

A

Arsencial war gas

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13
Q

How do Arsenics react?

A

React with the SH containing molecules (e.g. in Tissues)

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14
Q

How does Dimercaprol fight Arsenics?

A

It competes with the SH Group from the Tissues for !! Arsenicals –> Forming a stable and relative non toxic chelat complex

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15
Q

Dimercaprol and Metals (that form mercaptides with essential cellular SH groups) ?

A

Antidote against poisoning —including arsenic, gold, lead, and mercury (that act by combining with cellular sulfhydryl groups)

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16
Q

GSH

A
  • Tripeptide
  • Antioxidant
  • Isolated from yeast, muscle, and liver
    Role in the respiration and protects red blood cells against hydrogen peroxide (Reducing it to Water)
  • Cofactor for various enzymes
  • Formation of correct Disulfide Bonds in Proteins
  • Intracellular reductant (Reducing agent) –> Maintain SH groups of enzymes in a reduced state
  • Glutathione is not an essential nutrient for humans, since it can be synthesized in the body from the amino acids L-cysteine, L-glutamic acid, and glycine
17
Q

Tripeptide

A

Compound composed of three amino acids

18
Q

Linkage of GSH

A

Tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and the amine group of cysteine, and the carboxyl group of cysteine is attached by normal peptide linkage to a glycine

19
Q

Reducer

A

Substances that have the ability to reduce other substances (cause them to gain electrons)

20
Q

Disulfide bridgen Biochemistry

A

A single covalent bond between the sulfur atoms to two amino acids called cysteine

Can be considered as part of the primary structure of a protein

They are very important in determining the tertiary + quaternary structure of proteins

21
Q

What happens if GSH acts as a Reducing agent?

A

Its SH becomes oxidized and forms a disulfide ling with another GSH molecule

22
Q

Cysteamine

A

Thio-ethanol-Amine
Constituent of CoA
SH Group is a carrier of acyl radicals in citric acid cycle …

23
Q

How is CoA formed?

A

Activation of Panthothenic acid by Phosphorylation
Addition of Cystine
Adenylation by ATP

24
Q

Cysteine Key Step in Metabolism?

A

Oxidation to Cysteinsulfinate
Decarboxlyation –> Hypotaurine
Hypotaurine is oxidized –> Taurine

25
Q

Taurine

A

In bile together with bile acids

In brain

26
Q

Lipoic acid

A

Thioctic acid

Has a 1.2 Di Thiole Ring

27
Q

Course of oxidative decarboxylation of lipoic acid ?

A

Active disulfide form –> into red. form

Can be deoxidized by dihydrolipoyl dehydrogenase

28
Q

Allyl Disulfide

A

Aromatic component of Garlic oil

29
Q

Cystine

A

A crystalline, sulfur-containing amino acid that is formed from two molecules of the amino acid cysteine

Reconverted by Reduction –> addition of hydrogen

Abundant in skeletal and connective tissues and in hair

30
Q

Cysteine

A

Sulfur-containing nonessential amino acid

Organic chemistry (16 decks)

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