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Carbohydrates chapter 8 biochemistry
monosaccharides
93
Biochemistry
Undergraduate 3
02/09/2016

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Term
_________ are aldehyde or ketone derivatives of straight-chain polyhydroxy alcohols containing at least three carbon atoms
Definition
monosaccharides
Term
They are classified according to the chemical nature of their carbonyl group and the number of their C atoms?
Definition
Monosaccharides
Term
If the carbonyl group is an aldehyde, the sugar is an ___________
Definition
Aldose
Term
If the carbonyl group is a ketone, the sugar is a _____________
Definition
Ketose
Term
The smallest monosaccharides, those with three carbon atoms, are ___________
Definition
trioses
Term
Those with four, five, six, seven, etc. C atoms are, respectively,
________, ______________, _______________, ________________, etc.
Definition
tetrose, pentose, hexose, heptoses, etc.
Term
The aldohexose D-glucose has the formula _________
Definition
(C : H2O)6
Term
All but two of its six C atoms, C1 and C6, are chiral centers, so D-glu- cose is one of 24 16 possible stereoisomers.
True
False
Definition
True
Term
Are the L sugars mirror images of the D sugars?
Yes
NO
Definition
Yes
Term
Sugars that differ only by the configuration around one C atom are known as ___________ of one another.
Definition
epimers
Term
Are D-glucose and D-manose epimers with respect to C2?
Yes
No
Definition
Yes. google an image of these two sugars and compare...
Term
The most common aldoses include the six-carbon sugars _________, ______________, __________________.
Definition
glucose, monnose, and galactose.
Term
The pentose _____________ is a component of the ribonucleotide residues of RNA.
Definition
ribose
Term
The triode _________________ occurs in several metabolic pathways.
Definition
glyceraldehyde
Term
The most common ketone are those with their ketone function at C3.
True
False
Definition
False.
The most common ketoses are hose with their ketone function at C2
Term
The position of their carbonyl group gives ketoses one more asymmetric center than their isomeric aldoses.
True
False
Definition
False.
The position of their carbonyl group gives ketoses one less asymmetric center than their isomeric aldoses, so a ketohesose has only 2^3 = 8 possible stereoisomers (4 D
sugars and 4 L sugars).
Term
The most common ketoses are __________________, ________________, and _____________________.
Definition
dihydroxyacetone, ribulose, and fructose.
Term
Do monosaccharides vary in configuration and transformation?
yes
no
Definition
no.
monosaccharides vary in configuration and conformation
Term
Alcohols react with the carbonyl groups of aldehydes and ketones to form __________________ and ____________________.
Definition
hemiacetals and hemiketals.
Term
The biologically most common aldoses are _________________, ____________________, and _____________________.
Definition
D-Ribose (Rib), D-Glucose (Glc), and D-Mannose (Man).
Term
The biologically most common ketoses are ______________, and ___________________.
Definition
D-Ribulose and D-Fructose.
Term
What is the number of L-ketoses?
Definition
4 L sugars.
Term
The hydroxyl and either the aldehyde or the ketone functions of monosaccharides can likewise react intramolecularly to form cyclic hemiacetals and hemiketals.
True
False
Definition
True.
Term
The linear form of D-glucose yields the cyclic hemiacetal beta -D-fructofuranose.
True
False
Definition
False.
D-glucose yields the cyclic hemieacetal beta -D- glucopyranose.
Term
The linear form of D-fructose yields the hemiketal beta -D-fructofuranose.
True
False
Definition
True
Term
A sugar with a six-member ring is known as a ______________.
Definition
pyranose
Term
Sugars with five-membered rings are known as _________________.
Definition
furganoses.
Term
The cyclic forms of glucose and fructose with six- and five- membered rings are therefore known as ________________ and __________________.
Definition
glucopyranose and fructofuranose
Term
Cyclic sugars have three anomeric forms.
True
False
Definition
False
Cyclic sugars have TWO anomeric forms.
Term
When a monosaccharide cyclizes, the carbonyl carbon, called the ___________ _________, becomes a chiral center with two possible configurations.
Definition
anomeric carbon
Term
The pair of stereoisomers the differ in configuration at the anomeric carbon are called ____________.
Definition
anomers.
If you remember all of this you'll get an A.
keep going!
do at least 10 cycles.
Term
can a hexose or pentose assume pyranose or furganose forms?
yes
no
Definition
yes
Term
The _______ __________ of three- and four-membered rings makes them less stable than the linear forms.
Definition
internal strain
Term
The pyranose ring, like the cyclohexane ring, can assume a ________ conformation, in which the substituents of each atom are arranged tetrahedrally.
Definition
chair
Term
Of the two possible chair conformations, the one that predominates is the one in which the bulkiest ring substituents occupy ______________ positions rather than the more crowded _____________ positions.
Definition
equatorial axial
Term
Only ____________________ can simultaneously have all five of its non-H substituents in equatorial positions.
Definition
beta-D-glucose
Term
monosaccharides can readily shift is ____________________, because no bonds are broken in the process.
Definition
conformation
Term
Other changes in conformation, such as __________________, do not occur under physiological conditions without the appropriate enzyme.
Definition
epimerization
Term
Can sugars be modified and covalently linked?
no
yes
Definition
yes
you bet they do
Term
Because the cyclic and linear forms of aldose and ketoses do ______________, these sugars undergo reactions typical of aldehydes and ketones.
Definition
interconvert
Term
Oxidation of an aldose converts its aldehyde group to a carboxylic acid group, thereby yielding an ___________ _______ such as ____________ _______.
Definition
aldonic acid gluconic acid
Term
Oxidation of the primary alcohol group of aldoses yields _________ _______.
Definition
uronic acid
Term
Uronic acids can assume the _____________, ______________, and ___________ forms.
Definition
pyranose, furganose, linear
Term
Aldose and ketoses can be reduced under heavy conditions?
true
false
Definition
false.
aldose and ketoses can be reduced under mild conditions.
Term
Treatment with NaBH4 yields polyhydroxy alcohols known as ____________.
Definition
alditols
Term
_____________is a component of flavin coenzymes, and _______________ and the cyclic polyhydroxy alcohol ___________ are important lipid components.
Definition
Ribitol glycerol myoinositol
Term
_______________ is a sweetener that is used in "sugarless" gum and candies.
Definition
Xylitol
Term
Monosaccharide units in which an OH group is replaced by H are known as ________ _____________.
Definition
deoxy sugars
Term
The biologically dos important of these is _______________________, the sugar component of DNA's sugar-phosphate backbone.
Definition
beta-D-2-deoxyribose
Term
_____________ is one of the few L sugar components of polysaccharides.
Definition
L-Fucose
Term
In _______________ _________, one or more OH groups have been replaced by an amino group, which is often acetylated.
Definition
amino group
Term
The two most common amino sugars are ___________________, _____________________.
Definition
D-Glucosamine D-galactosamine
Term
________________ ________, which is derived rom N-acetylmannosamine and pyruvic acid.
Definition
N-Acetylneuraminic acid
Term
N-Acetylneuraminic acid is an important constituent of ______________ and _______________.
Definition
glycoproteins and glycolipids
Term
N-acetyleruaminic acid and its derivatives are often referred to as ____________ _______.
Definition
silica acids.
Term
In the cyclic form of N-Acetylneraminic acid, the pyranose ring incorporates the pyruvic acid residue and part of the mannose moiety.
Yes
NO
Definition
Yes
Term
______________ bonds link the Anomeric Carbon to other compounds.
Definition
Glycosidic
Term
The anomeric group of a sugar can _________________ with an alcohol to form alpha and beta glycosides.
Definition
condense
Term
The bond connecting the anomeric carbon to the alcohol oxygen is termed a __________________ __________.
Definition
glycosidic bond.
Term
N-Glycosidic bonds, which form between the ____________ carbon and an _____________, are the bonds that link D-ribose to purines and pyrimidines in nucleic acids.
Definition
anomeric amine
Term
Like peptide bonds, glycosidic bonds hydrolyze extremely fast under physiological conditions in the absence of appropriate hydrolytic enzymes.
True
False
Definition
False.
In the absence of appropriate hydrolytic enzymes, glycosidic bonds hydrolyze extremely slow.
Term
Can a anomeric carbon that is involved in a glycosidic bond freely convert between its alpha and beta anomeric forms?
Yes
NO
Definition
No.
An anomeric carbon that is involved in a glycosidic bond cannot freely convert between its alpha and beta anomeric forms.
Term
Saccharides bearing anomeric carbons that have not formed glycosides are termed ________________ __________.
Definition
reducing sugars.
Term
Saccharides bearing anomiric carbons that have not formed glycosides are termed reducing sugars, because the free aldehyde group that is in equilibrium with the cyclic form of the sugar reduces mild oxidizing agents.
True
False
Definition
True
Term
Identification of a sugar as nonreducing is evidence that it is a _________________.
Definition
glycoside.
Term
Disaccharides such as _____________ and ____________ consist of two sugars linked by specific glycosidic bonds.
Definition
lactose sucrose
Term
___________ and ______ are polymers of beta(1-->4)-linked glucose residues.
Definition
Cellulose chitin
Term
In __________ and ____________, glucose residues are linked mainly by alpha(1-->4) bonds.
Definition
starch glycogen
Term
___________________ and other large _____________________ typically have a gel-like structure.
Definition
Glycosaminoglycans heteropolysaccharides
Term
Polysaccharides, which are also known as ____________, consist of _________________ linked tighter by __________ bonds.
Definition
glycans monosaccharides glycosidic
Term
Polysaccharides are classified as _____________________ or ________________________ if they consist of one type or more than one type of monosaccharide.
Definition
homopolysaccharides heteropolysaccharides
Term
Polysaccharides, in contrast to proteins and nucleic acids, form __________ as well as __________ polymers.
Definition
branched linear
Term
Polysaccharides, in contrast to proteins and nucleic acids, form branched, as well as linear polymers, because ______________ linkages can be made to any of the _______________ groups of a monosaccharide.
Definition
glycosidic hydroxyl
Term
A complete description of an _________________ or polysaccharide includes the ____________, ______________ forms, and ____________ of all its component monosaccharide units.
Definition
oligosaccharide identities anomeric linkages
Term
Information about oligosaccharides or polysaccharides can be gathered through the use specific _______________________ and ______________________, enzymes that hydrolyze monosaccharides units in much the same way that exopeptidases and endopeptidase cleave amino acid residues from polypeptides.
Definition
exoglycosidases endoglycosidases
Term
________ measurements are also invaluable in determining both sequences and conformations of polysaccharides.
Definition
NMR
Term
Lactose and Sucrose are monosaccharides.
True
False
Definition
False.
Lactose and Sucrose are Disaccharides
Term
Oligosaccharides containing three or more residues are relatively rare, occurring almost in plants.
True
False
Definition
True
Term
___________________, the simplest polysaccharides, are more common.
Definition
Disaccharides
Term
Many disaccharides occur as the hydrolysis products of small molecules.
true
false
Definition
false.
Many disaccharides occur as the hydrolysis products of large molecules.
Term
__________ occurs, naturally only in milk, where its concentration ranges from 0 to 7% depending on the species.
Definition
Lactose
Term
The systematic name for lactose, ____________________________________________________, specifies its monosaccharides, their ring types, and how they are linked together.
Definition
O-beta-D-galactopyranosyl-(1-->4)-D-glucopyranose
Term
The symbol (1-->4) from O-beta-D-galactopyranosyl-(1-->4)-D-glucopyranose indicates that the glycosidic bond links C2 of the beta anomer of galactose to O4 of glucose.
True
False
Definition
False.
glycosidic bonds links C1 of the beta anomer of galactose to O4 of glucose.
Term
Lactose has a free anomeric carbon on its glucose residue and is therefore a reducing sugar.
True
False
Definition
True
Term
The most abundant disaccharide is _______________, the major form in which _____________________ are transported in __________.
Definition
sucrose carbohydrates plants
Term
Sucrose is familiar to us as common table salt?
yes
no
Definition
No
it is table sugar
Term
They systematic name for sucrose is _____________________________________.
Definition
O-alpha-D-glucopyranosyl-(1-->2)-beat-D-fructofuranoside
Term
The systematic name for sucrose, O-alpha-D-glucopyranosyl-(1-->2)-beta-D-fructofuranoside, indicates that the _______________ carbon of each ___________ (C1 in glucose and C2 in fructose) participates in the ________________ bonds.
Definition
anomeric sugar glycosidic
Term
The systematic name for sucrose, O-alpha-D-glucopyranosyl-(1-->2)-beta-D-fructofuranoside, indicates that eat anomeric carbon of each sugar (_____ in glucose and _____ in fructose) participates in the glycoside bonds.
Definition
C1 C2
Term
________________ and ________ are structural polysaccharides.
Definition
Cellulose chitin
Term
______________, the primary structural component of plant cell walls, accounts for over half of the carbon in the biosphere.
Definition
Cellulose
Term
Cellulose is a __________ polymer of up to 15,000 __________ residues linked by ___________ glycosidic bonds.
Definition
linear D-glucose beta(1-->4)
Term
_________ and other studies of cellulose fibers reveal that cellulose chains are ________ ribbons in which successive glucose rings are turned over _______ with respect to each other.
Definition
X-Ray flat 180-degrees
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