Lecture 19: carbohydrate structure Flashcards

1
Q

What are the 3 types of isomers?

A
  1. Constitutional
  2. Configurational
  3. Conformational
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2
Q

Describe constitutional isomers

A

The order of the atoms changes but the molecule formula stays the same. They are tautomers…

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3
Q

Describe stereoisomers

A

The atoms are connected in the same way but differ in spatial arrangements

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4
Q

Describe configurational isomers

A

have chiral carbons; can be divided into diastereomers and enantiomers

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5
Q

Define enantiomers

A

non-superimposable mirror images at ALL chiral centers (D vs L)

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6
Q

Define diasteeomers

A

isomers that are NOT mirror images, usually has more than one chiral carbon; can be divided into epimers and anomers

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7
Q

Describe the differences between a Fischer projection and the Hawthorne projections

A

Fischer projection are the linear versions of carbohydrates and the Hawthorne projections are cyclical versions of the carbohydrates

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8
Q

What are the different types or sugar derivatives?

A
  1. Fuctose
  2. Esters (phosphorylation)
  3. Oxidation/reduction (alcohols)
  4. N-linkages (amino sugar, nucleotides
  5. O-linkages (methylation, toxins)
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9
Q

Describe the structure of maltose

A

alpha-D-glucopyranosyl (1-4) and alpha-D-glucopyranose

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10
Q

Describe the structure of sucrose

A

alpha-D-glucopyranosyl (1-2) and Beta-D-fructofuranoside

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11
Q

Describe the structure of lactose

A

Beta-D-galactopyranosyl (1-4) and Beta-D-glucopyranose

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12
Q

Describe glycogen

A

alpha 1,4 glucose with an alpha 1,6 glycosidic linkages

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13
Q

Describe cellulose

A

Beta (1,4) linkages of glucose

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14
Q

Describe proteoglycans `

A

protein+glycosaminoglycans with the carbohydrate making the bigger portion pf the molecule. has repeating disaccharide units

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15
Q

Describe glycoproteins

A

carbs+proteins where the protein is the biggest portion of the weight of the molecule

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16
Q

Define conformational isomers

A

reversible rotation changes

17
Q

Describe fuctose

A

It is derived from galactose

Only L monosaccharide made and produced by animals

ABO Blood antigens

Excess free fuctose floating around in the blood causes bad shit to happen- liver damage, cancer, diabetes

18
Q

Describe phosphorylation in monosaccharide modification

A

phosphates are important reactive intermediates in carbohydrate metabolism, usually derived from ATP

-adds a negative charge to the molecule

(Name tells you where to put the phosphate)

19
Q

Describe oxidation in regards to monosaccharide modifications

A

oxidized at the carbonyl (the bond between the O in the ring and the C to the right) and can either make acids or lactones

20
Q

Describe reduction in regards to monosaccharide modification

A

reduction at the carbonyl makes alditols (the carbonyl that is at the top of the molecule (COOH) turns into an alcohol

21
Q

What is a common example of monosaccharide reduction in the body?

A

The reduction of D-glucose to D-glucitol, also called sorbitol, which can cause cataracts in the eye if it accumulates in the lens of the eye

22
Q

Describe amino sugars in regards to modified monosaccharides

A

found in branched polysaccharides (cell walls) and are commonly added to proteins

occur in N-linked glycosides

  • amine: NH2
  • acetyl: carbonyl attached to a methyl group
  • lactic acid CH(CH3)COO-
23
Q

What are the essential monosaccharides?

A
D-Glucose 
D-galactose
D-mannose 
D-xylose 
L-fuctose 
GlnNAc
GalNAc
Sialic Acid
24
Q

What are the roles of polysaccharides?

A
  1. Glucose storage (glycogen, amylose, cellulose)
  2. Structure (chitin is universal)
  3. Protein Diversity (glycoproteins, glycosaminoglycans, mucins)
25
Q

Describe chitin

A

Is a polysaccharide that is ESSENTIAL for structure

Beta-1,4-linkages of glucose

26
Q

Describe mucins

A

Sugar outweighs the proteins

provides lubrication which protects and hydrates

27
Q

Describe glycolipids

A

decorate cell membranes, and are used to recognize self and each other