Chapter 7 Flashcards
what are the 7 physiological functions of carbohydrates
1) source of energy
2) energy storage
3) structural roles
4) cellular interaction
5) cellular identification
6) information transfer (DNA and RNA)
7) signalling
what does carbohydrates mean
hydrate of carbon
what are the empirical formulas of carbohydrates
(CH2O)n where n is greater then or = to 3 (usually 3-6)
what are the two major classes of carbohydrates
-aldose (which have aldehyde group)
-ketoses (which have ketone group)
most monosaccharides have multiple…
asymmetric carbons
what designates a D or L sugar configuration
based on the configuration of the chiral carbon most distant from the carbonyl oxygen
what is the reference molecule for designation of D or L
D-glyceraldehyde
what group do all carbohydrates have
a carbonyl
what is contained in a ketone and a aldehyde
ketone is just a C double bond O and a aldehyde is a C double bond O and a H
what is the L and D configuration based on
the configuration of the chiral carbon most distant from the carbonyl oxygen
what side does the OH have to be on to be a D configuration
the right side
what side does the OH have to be on to be a L configuration
the left side
molecules with n chiral centers will have ____ sterioisomers
2^n
what are epimers
sugars that differ in configuration at one and only one chiral carbon
draw out a D-ribose
draw out a D-deoxyribose
draw out a D-glucose
draw out a D-mannose
draw out a D-galactose
draw out a D-fructose
draw out a dihydroxyacetone
draw out a D-glyceraldehyde
what has more chiral Cs aldose or ketosis
aldose has one more chiral C
what do longer carbohydrates tend to do in solution
longer carbohydrates (5 Cs and more) tend to be cyclized
what is longer C cyclized structures the result of
formation is the result of a reaction of an internal alcohol (hydroxyl group) with either:
1) an aldehyde (aldose) to form a hemiacital
2) a ketone (ketoses) to form a hemiketal
what is a stereoisomer
atoms are connected in the same order but differ in spatial arrangement
what is a epimer
they differ at one of several asymmetric carbon atoms
what is a isomer
they have the same molecular formula but different structures
what are constitutional isomers
they differ in the order of attachment of atoms
what is a enantomer
non superimposible mirror images
what are diastereoisomers
isomers that are not mirror images
what is anomers
isomers that differ at a new asymmetric carbon atom formed on ring closure
are all anomers epimers?
yes
are all epimers anomers?
no
what does cyclization of glucose involve
the C5 hydroxyl and the C1 aldehyde
in cyclization what happens when a C1 chiral is rendered
it produces two stereoisomers a and B
what is a anomeric carbon
the carbon that becomes chiral as a result of cyclization
what are the a and B forms of cyclization of eachother
they are a and B forms of each other
how can you tell if a carbohydrate molecule is a or B
you look at the carbon 1
if the OH is above the plane of the sugar its B
if the OH is below the plane of the sugar its a
cyclization produces a new ____ at the ____ resulting in two _____
chiral carbon, anomeric carbon, new stereoisomers (a and B)
what happen to a and B configurations in solution
they interconvert by a process called mutarotation
what is mutarotations intermedeate
it does from cyclization to linear intermediate back to cyclization
what does mutarotations represent
a change in configuration
what conformation fraction does glucose tend to be in solution
2/3 B-glucopyranose
1/3 a-glucopyranose
and less then 1% linear
what does the cyclization of fructose involve and what does it render
it involves the C5 hydroxyl and the C2 ketone
it renders C2 chiral (anomeric carbon) producing a and B sterioisomers
what ring does fructose exist in
both pyran and furan
where is B-fructopyranose found
in honey and its extreamly sweet