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39 Cards in this Set

  • Front
  • Back

these are organized by their number of carbon atoms and functional groups

carbohydrates

3 carbon sugars

trioses

4 carbon sugars

tetroses

sugars with aldehydes as their most oxidized group

aldoses

sugars with ketones as their most oxidized group

ketoses

sugars with the highest numbered chiral carbon with the -OH group on the right in Fischer projections are ____ sugars

D

sugars with the highest numbered chiral carbon with the -OH group on the left in Fischer projections are ____ sugars

L

D and L forms of the same sugar

enantiomers

nonsuperimposable configurations of molecules with similar connectivity

diastereomers

a subtype of diastereomers that differ at exactly one chiral carbon

epimers

a subtype of diastereomers that differ at the anomeric carbon

anomers

the ring formation of carbohydrates from their straight chain forms

cyclization

when rings form, the anomeric carbon can take on what 2 types of conformations?

alpha and beta

the new chiral center formed in ring closure; it was the carbon containing the carbonyl in the straight chain form

anomeric carbon

these anomers have the -OH on the anomeric carbon trans to the free CH2OH group

alpha anomers

these anomers have the -OH anomeric carbon cis to the free CH2OH group

beta anomers

these provide a good way to represent 3 dimensional structure

Haworth projections

when cyclic compounds shift from one anomeric form to another with the straight chain form as an intermediate

mutarotation

single carbohydrate units, with glucose as the most commonly observed monomer
monosaccharides

What 3 main reactions can monosaccharides undergo?

oxidation reduction, esterification, and glycoside formation

Aldoses can be oxidized to __________ and reduced to ___________.

aldonic acids, alditols

sugars that can be oxidized

reducing sugars

sugars with an -H replacing an -OH group

deoxy sugars

when a sugar reacts with a carboxylic acid and their derivatives, forming esters
esterification

the basis for building complex carbohydrates and requires the anomeric to link another sugar

glycoside formation
these form as a result of glycosidic bonding between 2 monosaccharide subunits
disaccharides

list 3 common disaccharides

sucrose, lactose, maltose
a polysaccharide that is the main structural component for plant cell walls and is a main source of fiber in the human diet

cellulose

these 2 starches function as a main energy storage form for plants

amylose and amylopectin

a polysaccharide that functions as a main energy storage for animals

glycogen

non-identical superimposable images of one another

enantiomers

number of stereoisomers with common back bone =

2^number of chiral carbons

How do you determine the rotation (+ or -) of a sugar?

experimentally
diastereomers that differ in configuration at exactly one chiral center
epimers
What is the most common electrophile on the MCAT?

carbonyl group

Due to ring strain, the only cyclic molecules that are stable in solution are what?

pyranose and furanose rings

ketose sugars are also __________________ and give positive Tollen's and Benedict's tests

reducing sugars

the rearrangement of bonds in a compound, usually by moving a hydrogen forming a double bond

tautomerization

this reaction forms a phosphate ester

phosphorylation