Carbohydrates and Related Compounds Flashcards
- polyhydroxy alcohols (either aldehyde or ketone)
- hydrates of carbon
- general formula: Cn(H2O)n
Carbohydrates
t/f: carbohydrates are the first products of cellular respiration
false. of PHOTOSYNTHESIS
simple sugars; have 1 sugar unit; cannot be further hydrolyzed
monosaccharides
Simplest synthetic sugar
Hydroxyacetaldehyde
Simplest natural aldose
Glyceraldehyde
Simplest natural ketose
Dihydroxyacetone
t/f: glyceraldehyde and dihydroxyacetone are both seen in glycolysis
true
favored/dominant (more active) fischer projection of carbohydrates
D-glucose
(cyclic config)
__________ : 6 membered ring
__________ : 5 membered ring
pyranose
furanose
configuration spotted by finding a carbon with two oxygens (basing from its position if up or down)
anomeric carbon / anomer
number of isomers: 2^n where n is the number of ?
(ex. glucose has 4 chiral carbons, thus glucose has 16 isomers)
chiral carbons
(recall)
isomer that differ in 2/more chiral carbon (e.g., arabinose and xylose (C2, C3))
diastereomer
(recall)
isomer that differ in only 1 chiral carbon, e.g., arabinose and ribose (C2), glucose and mannose (C2)
epimer
(recall)
isomer that are mirror images; all chiral carbons are switched, e.g., rhamnose and mannose
enantiomer
glucose, fructose, galactose, xylose are examples of?
MONOSACCHARIDES
- Aldohexose (CHO in C1)
- Reducing sugar as determined by BENEDICT’s Test
- Occurs as linear and cyclic
Glucose
glucose is also called
dextrose
blood sugar, physiologic sugar, grape sugar, corn sugar
glucose
only utilizable sugar in the blood
glucose
natural source of glucose
grapes
source of glucose
enzymatic hydrolysis of starch
glucose use: SMF
sweetening agent, mask unpleasant taste, flavor
purification of glucose
______________ : rigorously purified
pharmaceutic necessity : ________________
parenteral
less rigorous purification
D5W, D5NSS, D5LR
parenteral nutrient derived from glucose
parenteral glucose used in emergency room
to treat hypoglycemic patients that are unconscious, in comatose, or intoxicated with alcohol (alcoholic breath)
D50-50
pharmaceutic necessity glucose which is a syrupy liquid, almost colorless and taste sweet; sweetening agent
liquid glucose
pharmaceutic necessity glucose which is a crystalline sweetening agent
dextrose excepient
glucose which is an electrolyte replenisher
Calcium gluconate
t/f: liquid glucose is from the complete hydrolysis of lipids
false. INCOMPLETE hydrolysis of STARCH
glucose given in ethylene glycol poisoning (causes hypocalcemia) as supportive treatment
Calcium gluconate & gluceptate
glucose which is a calcium source
Calcium gluceptate
hematinic, glucose given for iron deficiency anemia
Ferrous gluconate
- In plants, sugar is transported in the form of sucrose through the ________ (food-conducting vessel).
phloem
- Water and minerals are absorbed from the roots and goes to the stem, leaves, etc. through the _________.
xylem
also called levulose / fruit sugar
Fructose
source of fructose: isomerization of glucose by ____________ through
the enzyme, _______________
Streptomyces, glucose isomerase
natural source of fructose
fruits and honey & hydrolysis of inulin
t/f: fructose in nature is in furanose form; isolated in liquid form as
pyranose
false. pyranose is in CRYSTALLINE form
use: food for diabetic people (cannot increase blood glucose level), for infant feeding formula
fructose
sweetest monosaccharide
fructose
Fructofuranose (natural)
Fructopyranose (____________)
crystalline
Identified by reducing agents like copper sulfate
reducing sugars
(reducing sugars)
CuSO4 + HAc
acidic medium
bArfoed
(reducing sugars)
CuSO4 + Na2CO3
basic medium
benedict’s
(reducing sugars)
CuSO4
Fehling’s
Glucose + CuSO4 to Gluconic acid + Cu2O
reducing sugar formula
o _______ - reducing agent
o _______ - mild oxidizing agent
o _______ - oxidation product; carboxylic acid
o _______ - reduction product; brick red ppt
Glucose
CuSO4
Gluconic acid
Cu2O
C4 epimer of glucose
galactose
source of galactose:
milk as ________
neuronal fibers as ____________
lactose
galactoceramides
t/f: galactose is convertible to glucose in the human body (enters glycolysis after 6 steps)
false. it is convertible to glucose BUT enter glycolysis AFTER 6 STEPS
disease that affects the body’s ability to convert galactose to glucose
Galactosemia
Test for galactose + positive result
Mucic acid test (violet ring)
Galactose + concentrated nitric acid
galactaric acid
__________________ converts galactose C1 and C6 to COOH to form galactaric acid (insoluble in water)
concentrated nitric acid (strong OA)
natural sources: corn cobs, straws, and heartwood of deciduous trees
xylose
wood sugar
xylose
natural source from materials soaked in dilute acids to hydrolyze xylan
xylose
use: diagnostic aid for intestinal malabsorption (absorbed but not metabolized; eg. Crohn’s, Celiac disease)
xylose
Composed of 2 monosaccharide units
disaccharides
t/f: disaccharides are formed via dehydration synthesis (forms N glycosidic bond)
false. it forms O/ETHER GLYCOSIDIC BONDS
Disaccharides: STM GLLC (its time, goodluck)
Sucrose (a 1,2)
Trehalose (a 1,1)
Maltose (a 1,4)
Gentobiose (a 1,6)
Lactose (b 1,4)
Lactulose (b 1,4)
Cellobiose (b 1,4)
Glucose + fructose
sucrose
also table sugar / saccharum
sucrose
a 1,2 glycosidic bond
sucrose
t/f: sucrose is a non-reducing sugar
true. it is negative on Barfoed’s, Benedict’s, Fehling’s or Tollen’s
natural sources of sucrose:
____________ : Saccharum officinale
____________ : Beta vulgaris
____________ : Acer saccharum
Sugar cane
Sugar beet
Sugar maple
Use: pharmaceutic necessity for syrups; demulcent; nutrient; preservative
sucrose
residual, dark colored syrup after crystallization process of sucrose
molasses
byproduct of table sugar production from sugar cane; “pulot”
molasses
t/f: sucrose, upon hydrolysis, yields a mix of glucose and fructose called invert sugar
true
sugar with equimolar amounts of glucose and fructose, which darkens due to fructose
invert sugar
t/f: invert sugar with a darker color results from a higher conc. of fructose compared to glucose (fructose > glucose)
true
Found in brown seaweed, widely distributed in fungi
trehalose
Glucose + glucose, α-1,1 glycosidic bond
trehalose
Produced in large quantities by the hydrolysis of starch during germination of barley
maltose
beer sugar / malt sugar
maltose
t/f: maltose is a component of soda and wine
false. component of BEER
source of bitterness in beer
Hops (Humulus lupulus) strobile
crude drug from beer which is a red brown powder
Lupulin
active ingredient of beer
Humulone, Lupulone
Glucose + glucose; α-1,4 glycosidic bond
maltose
sugar from fresh cow’s milk (Bos taurus)
lactose
milk sugar
lactose
lactose is formed from the crystalization of _______, which is a by-product of cheese production
whey
Glucose + galactose; β-1,4 glycosidic bond
lactose
lactose use
tablet diluent
absence of enzyme lactase or B-galactosidase (diarrhea, GI disturbance)
Lactose intolerance
Lactose derivation process
Milk (stand for hours) > churning (fat globules rise)
> Butter (top)
> Buttermilk (bottom)
> Skimmed milk > treat with rennin to form coagulum (casein)
> Cheese (solid)
> Whey (liquid) > whey has LACTOSE and inorganic salts
letting it stand, not disturbing it
churning
letting fat globules rise on top
creaming
milk without cream, non-fat milk
skimmed milk
coagulating enzyme found in the stomach of mammals
renin
partially evaporated milk
condensed milk
milk evaporated with malt extract from barley (Hordeum vulgare)
malted milk
alcoholic beverage made from fermented mare’s milk made by nomads of central Asia
Kumyss
Synthetic sugar from the TAUTOMERIZATION of lactose
Lactulose
alkaline rearrangement of a ketone to an enol
Tautomerization
Use: Laxative and decrease blood ammonia conc.
lactulose
mechanism of lactulose as laxative
- Poorly absorbed (stays in GIT); bacteria (colon) converts it to acetic acid and lactic acid
- Both acids are GI irritants, ↑ peristalsis
mechanism of lactulose in decreasing blood NH4 in portal-systemic encepalopathy
- Acidified stools trap ammonia as NH4+ so
↓reabsorption, ↓blood ammonia
constitutional isomers of organic compounds that readily interconvert in a rapid equilibrium
Tautomers
commonly results in the relocation of a proton relevant to the behavior of amino acids and nucleic acids
tautomerism
most common tautomeric relation in organic chemistry
keto-enol
Have 3-10 sugar units
oligosaccharides
oligosaccharides: MaDe GRafSta
Maltotriose
Dextrin
Gentianose
Raffinose
Stachyose
Glucose + glucose + glucose
Maltotriose
products of partial hydrolysis of starch
(amylase, glucosidase)
limiting dextrin
causes the browning of bread
limiting dextrins
limting dextrin mechanism
starch > amylase > LIMITING DEXTRINS > a-glucosidase > glucose
amylase degrade _____________ bonds while a-glucosidase degrades ___________ bonds
α-1,4
α-1,6
Inhibits conversion of limiting dextrin (not absorbed, defecated/diarrhea) to glucose (absorbed)
α-glucosidase inhibitors
Inhibit post-prandial (after eating) increase in glucose levels (anti-DM)
α-glucosidase inhibitors
examples of α-glucosidase inhibitors
Acarbose, Miglitol
AE of dextrins
flatulence, hepatotoxicity
t/f: dextrin is used as positive control
to check euglycemic property or amylase and α-glucosidase inhibitory activity
true
Glucose + glucose + fructose OR Sucrose + glucose
gentianose (from Gentiana spp)