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CHEM/OCHEM (MCAT) > Biological Molecules > Flashcards

Biological Molecules Flashcards

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1
Q

What is the suffix that designates a carbohydrate?

A

-ose

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2
Q

What is the difference between oligosaccharide and polysaccharide?

A

oligosaccharide = neither simple nor complex carbs, usually containing 3-10 repeating monomers

polysaccharide = complex carbs, made of >10 monomers

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3
Q

What are the 2 classifications of open-chain or linear forms of monosaccharides?

A

aldoses and ketoses

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4
Q

What is the difference between a D (+) sugar and an L (-) sugar? (consider fisher projection structures)

A

D sugar: highest number chiral carbon -OH on right

L sugar: highest number chiral carbon -OH on left

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5
Q

The human body has enzymes that recognize ______ sugars.

a) D
b) L

A

a) D

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6
Q

TRUE or FALSE: D and L correspond to R and S.

A

FALSE –> no relation at all

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6
Q

Draw the D-glucose and L-glucose enantiomers. Pay attention to the bottom cross.

A

ye draw it bruh

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7
Q

List the following from highest to lowest priority group (when designating D or L):

carboxylic acid, alcohol, carbonyl

A

carboxylic acid > carbonyl > alcohol

hint: most oxidized is highest priority and least oxidized is lowest priority

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8
Q

What is the “bottom cross rule” in terms of designating D and L? When can this rule be applied?

A

bottom cross rule = the direction of OH on the bottom cross of the sugar (in a fisher projection) determines D or L (i.e. if OH on left, then L enantiomer)

*can only be applied if highest priority carbon is at the top of the fisher projection diagram

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9
Q

How do you determine if 2 sugar molecules are enantiomers?

A

OPPOSITE absolute configuration of ALL chiral carbons

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10
Q

How do you determine if 2 sugar molecules are diastereomers?

A

> /= 1 chiral carbons with OPPOSITE absolute configuration AND >/= 1 chiral carbons with SAME absolute configuration

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11
Q

How do you determine if 2 sugar molecules are epimers?

A

EXACTLY 1 chiral carbon with opposite absolute configuration AND >/= 1 chiral carbon with the SAME absolute configuration

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12
Q

What reagents need to be added to an aldehyde/ketone to form a hemiacetal/hemiketal?

A

alcohol (with desired functional (R) group) + acid

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13
Q

TRUE or FALSE: even if a carbonyl/hydroxy group is located on the same molecule as an aldehyde/ketone, an intramolecular nucleophile addiction cannot take place

A

FALSE –> intramolecular reaction can occur to yield cyclic hemiacetal/hemiketal

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14
Q

TRUE or FALSE: furanose (5 member ring) is more stable than pyranose (6 member ring)

A

FALSE –> pyranose (6 member ring) is more stable than furanose (5 member ring)

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15
Q

How do you identify the anomeric carbon in a cyclic structure?

A

anomeric carbon is the only carbon with 2 oxygen groups attached to it

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16
Q

What is the difference between the alpha and beta anomer of D-glucose (structurally)? Which one is the major anomer and which one is the minor anomer? Draw the structures.

A

alpha = minor = OH at C1 is TRANS to C2OH at C5

beta = major = OH at C1 is CIS to C2OH at C5

did you draw it lol (hint: change the configuration at C1 of glucose)

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17
Q

Why is the beta-anomer of D-glucose major in comparison to the alpha-anomer?

A

beta is more stable because all substituents are equatorial (less sterically hindered)

18
Q

How is Haworth projection (for chair/planar conformation) related to Fisher projection?

A

OH groups pointing LEFT in Fisher go UP in Haworth

OH groups pointing RIGHT in Fisher go DOWN in Haworth

19
Q

In the Haworth projection for sugars, which direction does the CH2OH on C5 point for D sugars? What about for L sugars?

A

D sugar: CH2OH on C5 points UP

L sugar: CH2OH on C5 points DOWN

20
Q

Draw the D glucose fischer projection and the beta D glucose haworth projection.

A

now go check it

21
Q

What reagents should be added to form an acetal/ketal from a hemiacetal/hemiketal?

A

alcohol (with new R group) and acid

hint: same as from acetaldehyde/ketone to hemiacetal/hemiketal

22
Q

What reagents can be used to reduce a sugar?

A

Tollens’ reagent and Benedict’s reagent

23
Q

What kind of linkage is yielded when forming disaccharides?

A

1,4-linkage (glycosidic)

24
Q

What monomers make up lactose? What kind of bond links the monomers?

A

D-galactose + D-glucose

beta-1,4 glycosidic bond

25
Q

What monomers make up maltose? What kind of bond links the monomers?

A

2 D-glucose molecules

alpha-1,4’ glycosidic bond

26
Q

What monomers make up sucrose? What kind of bond links the monomers?

A

D-glucose + D-fructose

1,2’-glycosidic bond (between both anomeric carbons)

27
Q

What monomers make up cellulose? What kind of bond links the monomers?

A

chain of glucose molecules

beta-1,4’ glycosidic bond

28
Q

What monomers make up amylose? What kind of bond links the monomers?

A

chain of glucose molecules

alpha-1,4’ glycosidic bond

29
Q

What monomers make up amylopectin? What kind of bond links the monomers?

A

BRANCHED chain of glucose

alpha-1,4’ glycosidic bonds + alpha-1,6’ glycosidic bonds (at branching points)

30
Q

What monomers make up glycogen? What kind of bond links the monomers?

A

BRANCHED chain of glucose

alpha-1,4’ glycosidic bonds + alpha-1,6’ glycosidic bonds (at branching points)

(hint: same as amylopectin??? …unless I read the book wrong :(((( )

31
Q

TRUE or FALSE: amino acids can also be designated with D or L configuration

A

TRUE –> look at NH2 direction instead of OH direction in Fischer projection

32
Q

____ amino acids are found in animal proteins.

a) D
b) L

A

b) L

33
Q

What is the name of the reaction for breaking down a triglyceride into its glycerol backbone and fatty acid tails? What reagent is needed for this reaction to occur?

A

lipolysis/saponification

H2O or -OH

34
Q

What does the structure of triglyceride consist of? Draw it.

A

glycerol backbone and 3 fatty acid tails

yeah now draw it

35
Q

What does the structure of phospholipids consist of? Draw it?

A

glycerol, 2 fatty acid tails, one phosphate group

did you draw it?

36
Q

What does the structure of sterols consist of? Draw a steroid and then draw a sterol.

A

4 rings

see page 211 in chem cc for the diagrams

37
Q

What is the difference between a steroid and a sterol?

A

steroid is very hydrophobic

sterol has an OH group (alcohol)

38
Q

be able to recognize the terpene structures on page 212 of chem cc!

A

go look…do you recognize them?

39
Q

What kind of bond forms between 2 nucleic acids?

A

phosphodiester link

40
Q

what are the two things that carbohydrates need to be able to do in order to be a reducing sugar

A
  1. convert to the open chain form

2. have an aldehyde group

41
Q

what are examples of non reducing sugars

A

acetals and glycosides

42
Q

true or false - all aldoses are reducing sugars

A

true

CHEM/OCHEM (MCAT) (10 decks)

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