chem ch. 20 Flashcards
carbohydrates or polyhydroxy are
aldehyde or ketones
carbohydrates end in…
ose
simple monosaccaharide has…
3-7 carbons
triose
monosaccharide with 3 carbons
tetrose monosaccharide
4 carbons
pentose
5 carbons
hexose
6 carbons - glucose in this category
heptose
7 carbons
aldose
when they have aldehyde functional gropu
ketose
when they have ketone functional group
fischer projection
This is the straight chain, not coiled/cyclic. C=O aldehyde or ketone should be at the top.
every sugar has a…
chiral carbon
if you have aldose with 4C, how many will be chiral?
2 of them will be chiral
if you have pentose, 5 C, then you have how many chiral carbons?
3, it’s always 2 less with aldos
ketoriose has no…
chiral center
top and bottom C are not..
chiral. they are attached to H2OH and H
ketose chiral is…
3 less than the total number of Cs
ketotetrose has how many chiral?
1 chiral. 3 less than the total C - 4
isomers types
stereoisomers and structural
stereoisomer can be either…
1) enatiomer
2) diastereomers
for sugars, nature uses D or L? (nature Digs sugar)
D - sugars (amino acid is the opposite, it’s L for amino acids)
if OH group is on the right, it’s
D. If it’s left, it’s L
two stereoisomers that are not mirror images of each other are called…
diastomers
sugar reactions - aldehyde
aldehyde - oxidized to carboxylic acid and can be reduced to alcohol
sugar w/ aldehyde naming when oxidized (sugar ate the oxi)
D-glucose becomes D-gluconate
any sugar reduced is called…
reducing sugar
all aldoses are…
reducing sugars (because they can be oxidized)
ketone can’t be…
oxidized
BUT*****ketoses in basic solution can be…
oxidized (they normally cannot because they don’t have a free bond) - it’s called tautomerization. The double bond is literally moved from the second carbon to the top carbon.
all simple sugars, including all aldhydes and ketose in BASIC solution (OH-) are…
reducing sugars.
sugars can also do…
reduction reaction - ie - aldehydes reduced to primary alcohol and ketones reduced to secondary alcohol
haworth structure
coiled together
aldehyde + alcohol =
hemiacetal
internal hemiacetal formation will become
cyclic
C # 1 is the…
anomeric carbon - ONLY in cyclic structure, not Fischer
if OH is pointing up (on top), it’s
beta
if OH is pointing down (on the bottom), it’s
alpha
in the solution, alpha and beta can be…
converted to each other (first converted to Fischer (straight chain) - then either alpha or beta)
mutarotation
alpha can be converted to B and vice versa in solution
look at C number one, and you can tell if it’s
alpha or beta depending on how the OH is arranged - either on top or on bottom
D-glucose
also called dextrose or blood sugar. Aldohexose. D-glucose is most abundant
anything cyclic with anything other than C is called.
heterocylic
D-glucose is found in…(what foods) (FCH glucose)
fruit, honey, corn syrup
building block of all polysaccharides is…
D-glucose
D-glucose can be stored as…
gylcogen in our liver
D-galactose (this is an aldohexose) (milk of the galaxy)
known as milk sugar - in milk is lactose
important component of brain and nervous system (brain is a galaxy)
D-galactose
galactosemia
deficiency of enzyme to covert galactose to glucose. as a result, toxic level of galactose in blood, kidney failure. treatment is galactose free diet.
D-fructose - what food can you find it in?
fruit sugar, honey
is sugar soluble or insoluble?
soluble and can make H bonds
D-ribose (RNA) and deoxyribose (DNA)
main compenent of DNA and RNA
glycosidic bond
the bond (oxygen) between two carbons in disaccharide
disaccharides (3 of them) (die slm)
1) maltose
2) lactose
3) sucrose
lactase - think, not lactose
enzyme that breaks down lactose - if you don’t have it, you are lactose intolerant
sucrose is known as…
table sugar (alpha 1 and 2 link)
polysaccharides
polymer of glucose only*****
one that is digestible by humans is starch
starch (amy loves starch)
A) amylose (20%) - this is the soluble part - non-branched
B) amylopectine (80%) - branched
beans, wheat, grains
glycogen
found in animals, polymer of glucose, can be stored in liver
cellulose - covered in cellulose (plants in the frat)
most abundant polysaccharide on earth, but humans can’t use it. Fibrous. B (1,4)
saccharides can be any of the following: (1, 2 or 3)
monosaccharides, disaccharides or polysaccharides
general name for glyceraldehyde
aldotriose. Aldotriose can be used for different sugars, it’s just a general name.
in sugars, every carbon aside from the functional group has to have…
an OH group
the last C in all sugars looks like…
CH2OH
ketone with 3 Cs (ketotriose) is the only one that…
doesn’t have chiral center. Ketotriose doesn’t exist in nature, btw
fructose is a ketose with…(we’re left with 3 fruits)
6 carbons, and the 3rd C the OH is on the left. All other OHs on the right
glucose is an aldose with…(glucose is the 3rd house on the left)
6 carbons, and the 3rd OH is on the left, the other OHs on the right
for mirror image, DO not change any carbons that…
are not chiral. Only switch the chiral carbons (ie - don’t switch the top and bottom carbons)
enantiomers are…
stereoisomers that are mirror images - just means that they are mirror images of each other
the next to last carbon used that is attached to the D or L is called..
penaltimate carbon
if you have more than one chiral carbon, how do you determine D or L?
use the chiral carbon furthest from the functional group, so it will be the second from the bottom
remember, aldehydes can be oxidized to..
carboxylic acid
remember, aldehydes can be reduced to…
alcohols
any sugar that can be oxidized, is called..
a reducing sugar. A reducing sugar is anything that can be changed to a carboxylate
sugar alcohols are what structure?
hayworth structure
fischer projection only used for
straight chain sugars
when you make sugar alcohols into a circle, you’re joining which carbons together?
1 and 5, and 6 is sticking out on top - (if there are 6 carbons - if there are 7, then it’s the 6th carbon)
in sugar alcohols, the OH from the 5th carbon (or second to last)
is the one that joins with aldehyde to form the hemiacetal. The double bond from the aldehyde becomes a single bond, and it turns into OH
to identify D or L, look at the…
C furthest away from the carbonyl group (obviously not the last one, but the one with the last OH group)
d-glucose is the building block…
of all polysaccharides
glucose can be stored as…
glycogen in our body
every single sugar has to be converted to…
glucose for us to use it
galactosemia
deficiency of the enzyme to covert gala - glu. as a result, toxic level of galactose in blood. treatment is galactose free diet.
sugar is insoluble or soluble?
very soluble bc of the OH groups
in diastomers, the difference is…
OH group is on different side for at least one chiral center. that’s it.
where to place OH group in ring (up or down) (downright confusing)
right is down, left is up
alpha is going…
down
beta is on..
top
left (L) OH is which way?
up
right (D) OH is which way? (downright confusing)
down
maltose (malts only need 2 glucoses)
2 glucose
lactose (milk for GG)
1 glucose + 1 galactose
sucrose (fg sucrose is good)
fructose and glucose
gyclosidic bond is labeled with what carbons?
the carbons that are linked together, can be 1,4 or 1,2 etc.
in glcyocidic bond, if the first carbon is alpha, label it
alpha 1,4. if it’s beta, do beta 1,4
2 disaccharides combined form…
acetal (a C attached to 2 oxygen, an acetyl group, and an H)
maltose - alpha and beta info. (malt is god)
alpha 1,4
lactose - alpha and beta info. (frat lactose intolerant)
beta 1,4
sucrose - alpha and beta info. (sucrose is the first god, and FG it’s good) and what’s it’s made of
alpha 1,2 anomeric link fructose and glucose
glycogen - alpha or beta info. (god needs glycogen)
alpha 1,4 link, some alpha 1,6 but usually 1,4
