BIOCHM E2 C7

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BIOCHM E2 C7
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BIOCHM E2 C7
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  1. NAME 5 CLASSES OF Carbohydrates
  2. Monosaccharides
    • Disaccharides
    • Polysaccharides
    • Glycoconjugates
    • The Sugar Code
  3. ----------- are the most abundant biomolecule in nature
    Carbohydrates
  4. Sugars with an aldehyde functional group are ------
    aldoses
  5. Sugars with an ------ functional group are ketoses
    ketone
  6. ------------------ or simple sugars, are polyhydroxy
    aldehydes or ketones
    Monosaccharides
  7. ALDOSE OR KETOSE?
    ALDOSE
  8. ALDOSE OR KETOSE?

    KETOSE
  9. WHAT'S THE DIFFERENCE BETWEEN ALDOSE AND KETOSE?
  10. Carbohydrates are precursors for other biomolecules. EXPLAIN WHY/HOW.
    THEY CAN CONVERT TO OTHER PRODUCTS. PROTEINS---> SUGARS
  11. Most abundent carbihydrates in living cells are:
    ---- & -----.
    hexoses and pentoses.
  12. Trioses OR hexoses...WHICH ONE IS FOUND IN DNA?
    HEXOSES
  13. T OR F ?
    Class names often combine information about carbon number and functional group
  14. WHAT IS THIS? MUST DRAW FOT THE TEST!!
    • D-RIBOSE.
    • COUNT THE CHIRAL CENTER. THERE'S 5.
  15. WHAT DOES D-RIBOSE LOOK LIKE?
    HOW MANY CHIRAL CARBONS?
    • 5 CHIRAL CARBONS.
    • MUST DRAW FOR TEST!!!!
  16. WHAT IS THIS?
    • ALDEHYDE FORMATION.
    • FOUND ON GLYCERALDEHYDE.
  17. HOW MANY CHIRAL CARBONS IN D-GLUCOSE?
    MUST DRAW FOR TEST !!!!
    • SIX
  18. WHAT IS IT? MUST DRAW FOR TEST!!!!
    D-GLUCOSE
  19. T OR F?
    An increase in the number of chiral carbons increases the number of possible
    optical isomers
    TRUE
  20. "2n"...WHAT DOES THE "n" MEAN?
    "n" IS THE NUMBER OF CHIRAL CARBONS.
  21. 4 chiral centers = ? isomers
    16
  22. WHAT'S THE DIFFERENCE BETWEEN A ALDOSE AND KETOSE?
    • A chain-form monosaccharide that has a carbonyl group (C=O) on an end carbon forming an aldehyde group (-CHO) is classified as an aldose.
    • When the carbonyl group is on an inner atom forming a ketone, it is classified as a ketose.
  23. Almost all naturally occurring monosaccharides are WHAT FORM? D OR L?
    D FORM
  24. In optical isomers, the ------ carbon is the asymmetric
    carbon farthest from the carbonyl carbon
    • ´╗┐REFERENCE CARBON.
  25. WHAT THE HELL IS THIS? MUST DRAW FOR TEST!!!!
    D-GALACTOSE
  26. MUST BE ABLE TO DRAW D-GALACTOSE FOR THE TEST!!!
  27. Almost all naturally occurring monosaccharides
    can be considered to be derived from D-glyceraldehyde
    or ------------- ------------------.
    nonchiral dihydroxyacetone
  28. ------------ are stereoisomers that are mirror
    images (D vs. L)
    • Enantiomers.
  29. ------------- stereoisomers that are not enantiomers
    Diastereomers.
  30. Diastereomers that differ at a single chiral carbon are ---------- (e.g., D-riboseand D-arabinose) See arrows.
    • epimers.
  31. T OR F?
    Arabinose is an epimer of
    ribose (or ribose is an epimer of arabinose).
    TRUE
  32. Sugars with four or more carbons exist primarily in WHAT FORM?
    cyclic forms (ring forms)
  33. Ring formation occurs because aldehyde and ketone groups react reversibly with
    hydroxyl groups in an aqueous solution to form
    ------- & ---------.
    hemiacetals and hemiketals
  34. hemiacetals and hemiketals.
    HOW ARE THEY FORMED?
    • Ring formation occurs because aldehyde and ketone groups react reversibly with
    • hydroxyl groups in an aqueous solution.
  35. HOW IS A HEMIACETAL FORMED?
    • RING STRUCTURE FORMED BY ALDEHYDE AND ALCOHOL IN AQUEOUS SOLUTION.
  36. HOW IS A HEMIKETAL FORMED?
    • RING STRUCTURE FORMED BY KETONE AND ALCOHOL IN AQUEOUS SOLUTION.
  37. Two possible diastereomers that form because of cyclization are called --------.
    anomers
  38. two possible diastereomers that
    form because of cyclization are called anomers.
    HOW?
    • Hydroxyl (-OH) group on hemiacetal
    • occurs on carbon 1 and can be in the up position (above ring) or down position (below ring).
  39. In the D-sugar form, when the anomer
    hydroxyl is up it gives a -- ------- FORM.
    • b-D-anomeric form
    • (left in Fischer projection) .
  40. In the D-sugar form, when the anomerhydroxyl is up it gives a -- ------- FORM.
    • a-D-anomeric form
    • (left in Fischer projection) .
  41. Haworth Structure of the A-D-Glucose.
    1. IS THE -OH ON THE FIRST CARBON DOWN OR UP? MUST DRAW FOR TEST !!!!
    2. WHAT IS IT'S FORMAL NAME IN THE HAWORTH STRUCTURE FORM?
    • DOWN.
    • a-D-glucopyranose (6 SIDED RING)
  42. Haworth Structure of the B-D-Glucose....IS THE -OH ON THE FIRST CARBON DOWN OR UP?
    MUST DRAW FOR TEST!!
    • UP. REMEMBER BOAT.
  43. Five-membered rings are called -------.
    • furanoses
    • (fructose)
  44. Six-membered rings are------
    • pyranoses
    • (glucose)
  45. Cyclic form of fructose is ----------- ,
    while glucose in the pyranose form
    is --------------.
    • fructofuranose
    • glucopyranose
  46. BE ABLE TO DRAW D-FRUCTOSE IN A FISHER FORM.
  47. MUST BE ABLE TO THE ALPHA & BETA FORM FROM THIS:
  48. WHAT IS THE "BUSINESS END" OF A MONOSACCHARIDE?
    • ANOMERIC END...REACTIVE...CARBOXYL OR ALDEHYDE....FORMS PRODUCTS.
  49. This spontaneous process,--------- produces
    an equilibrium mixture of a- and b-forms
    in both furanose and pyranos ring
    structures.
    • mutarotation.
    • Open chain form can participate in redox reactions-Bendicts test.
  50. 3 IMPORTANT MONOSACCHARIDES ARE NOTED IN LECTURE. GIVE THE HAWORTH FORM NAME OF THEM.
    • a-D-glucopyranose (GLUCOSE AKA DEXTROSE)
    • b-D-fructofuranose (FRUCTOSE)
    • a-D-galactopyranose ( GALACTOSE)
  51. The primary fuel for living cells.
    Preferred energy source for brain cells and cells without mitochondria (erythrocytes).
    We get a ton of it from HFCS (high fructose corn syrup and break down of starch).
    WHAT THE HELL IS IT?
    GLUCOSE (D-GLUCOSE) (DEXTROSE)
  52. HFCS—high fructose corn syrup—processed mixture of ------- & --------used as as a
    sweetener. (combine to give ratios similar to table sugar—sucrose).
    glucose and fructose
  53. On a per gram basis, it is twice as sweet as sucrose, therefore it is often used as
    a sweetening agent in processed food
    FRUCTOSE (D-FRUCTOSE)
  54. -----------can interconvert glucose and galactose
    Epimerase
  55. --------------- a genetic disorder resulting from a missing enzyme in galactose
    metabolism
    Galactosemia
  56. -------necessary to synthesize a variety of important biomolecules (found in milk in
    lactose). Important biomolecules include: lactose, glycolipids, phospholipids, and glycoproteins
    Galactose
  57. Reaction and Modification of Monosaccharides the
    ---- & ------ groups can undergo several chemical reactions.
    carbonyl and hydroxyl
  58. Reaction and Modification of Monosaccharides
    NAME THE TOP 5
    • oxidation,
    • reduction,
    • isomerization,
    • glycoside formation,
    • glycosylation reactions
  59. T OR F?
    All monosaccharides are reducing sugars and some di and polysaccharides
    are as well as long as anomeric carbon not in fixed linkage
    TRUE
  60. Sugars that can reduce another species (they become oxidized in the process) such as
    Cu+2 to Cu+1 (Benedict’stest) are called -------?
    reducing sugars
  61. monosaccharides may readily undergo several -------- reactions in the presence of metal ions or
    certain enzymes.
    OXIDATION (GAIN OXYGEN)
  62. Oxidation of the aldehyde group yields ----- -----.
    aldonic acid
  63. Oxidation of the terminal CH2OH
    group yields ----- -----.
    uronic acid
  64. Oxidation of both the aldehyde and the CH2OH groups yields ----- ------.
    aldaric acid
  65. THE OXIDATION PRODUCTS OF GLUCOSE INCLUDE WHAT?
    NAME 3
    • aldonic (OX OF -CHO)
    • aldaric (OX OF -CH2OH)
    • uronic acid (OX OF BOTH)
  66. 2 MAIN SUGARS IN HFCS
    (high fructose corn syrup)
    BREAK DOWN STARCH....GET GULCOSE AND MIX WITH FRUCTOSE....TA DA HFCS!
  67. ----- can be produced if the carbonyl groups of aldonic or uronic acids react with an OH group in the same molecule.
    • A lactone
    • (cyclic ester)
  68. Lactones are readily produced in nature, for example
    ---------.
    • L-ascorbic acid
    • (vitamin C) a powerful reducing agent that protects cells from reactive oxygen and
    • nitrogen species.
  69. ---------- are produced by the reduction of aldehyde and ketone groups of monosaccharides
    ALDITOLS (Sugar alcohols)
  70. WHAT THE DIFFERENCE BETWEEN ALDITOLS AND ALDONIC ?
    • ALDITOLS....reduction of aldehyde and ketone GROUPS.
    • .
    • ALDARIC...OX OF BOTH aldehyde and ketone
  71. Sugar alcohols (alditols) are produced by the ------ of aldehyde and ketone groups of monosaccharides
    reduction
  72. EXAMPLE OF ALDITOL (SUGAR ALCOHOL) USED IN FOOD AND PHARMACEUTICALS.
    SORBITOL. HELPS PREVENT MOISTURE LOSS.
  73. REDUX OR OX?
    Reduction (gain hydrogens)
  74. D-glucose incubated in an alkaline (STRONG BASE) solution for several hours produces two isomers: D-mannose
    and D-fructose...KNOWN AS WHAT?
    ISOMERIZATION
  75. DEFINE EPIMERIZATION
    • 2 MONOSACCHARIDES, DIFFERENT BY ON CHIRAL CARBON.
  76. T OR F ?
    The transformation of glucose to fructose is an aldose-ketose interconversion
    TRUE
  77. ------Glycosidic linkages
    form between oligosaccharides and the side chain amide nitrogen of certain
    asparagine residues
    • N
    • BONDS TO "N" OF THE NH3.
  78. ------ Glycosidic linkages attach glycans to
    the side chain hydroxyl of serine or threonine residues, or the hydroxyl oxygens of
    membrane lipids
    • O.
    • SERINE -OH
  79. POST TRANSLATION MODIFICATIONS ARE A RESULT OF WHAT?
    • Glycosylation Reactions attach
    • sugars or glycans (sugar polymers) to proteins or
    • lipids—i.e. post translation modifications
  80. Catalyzed by -------- ---------- glycosidic
    bonds are formed between anomeric
    carbons in certain glycans and
    oxygen or nitrogen of other types of molecules, resulting in N- or O-glycosidic bonds
    glycosyl transferase
  81. IS THIS GLUCOSEAMINE?
    • NO. Galactoseamine. YOU MUST KNOW GLUCOSEAMINE FOR TEST! FLIP -OH ON CARBON 4 DOWN.
  82. WHAT 2 AMINO SUGARS ARE THE MOST COMMON AND OFTEN ATTACHED TO PROTEINS OR LIPIDS?
    • D-Glucosamine
    • and D-galactosamine
  83. DEFINE Deoxy Sugars.
    • Monosaccharides that have an –OH replaced by an –H or –CH3.
    • EX: Fucose & 2-deoxy-D-ribose
  84. NAME 2 MONOSACCHARIDE DERIVATIVE GROUPS
    DEOXY AND AMINO SUGARS
  85. In polysaccharides, large numbers of monosaccharides are linked together through ------ ----- OR ------ ------.
    • acetal linkages or glycosidic linkages.
    • BOTH MEAN THE SAME THING. ACETAL LINKAGE IS THE FORMAL WAY OF STATING IT.
  86. Naming of glycosides specifies the sugar component,
    Acetals of glucose and fructose are ---- & ------.
    • glucoside and fructoside.
    • REMEMBER THAT GLYCOSIDIC LINKAGE AND ACETAL LINKAGES ARE THE SAME THING.
  87. If an acetal linkage is formed between the hemiacetal
    hydroxyl of one monosaccharide and the hydroxyl of another, this forms a -------.
    disaccharide.
  88. THE BLUE BOX IS AN EXAMPLE OF WHAT?
    • GLYCOSIDIC LINKAGE.
    • Acetal of glucose ....glucoside.
  89. In ----------, large numbers of monosaccharides
    are linked together through acetal
    linkages or glycosidic linkages
    polysaccharides
  90. --------- --------: hemiacetals and hemiketals
    react with alcohols to form the corresponding acetal and ketal
    Glycoside Formation
  91. Glycoside Formation- hemiacetals and hemiketals
    react with alcohols to form the corresponding ------ & -------.
    acetal and ketal
  92. When the cyclic hemiacetal or hemiketal form
    of the monosaccharide reacts with an alcohol, the new linkage is a--------- ---- AND THE COMPOUND IS A ----------.
    glycosidic linkage and the compound a glycoside
  93. 2 monosaccharides
    linked by a glycosidic bond IS CALLED WHAT?
    DISACCHARIDES
  94. GLYCOSIDIC BONDS CCAN OCCUR AT WHAT CARBON POSITIONS?
    • ALL OF THEM! KNOW THE CARBON POSITIONS!!
  95. LABEL AND IDENTIFY THIS. MUST KNOW FOR TEST!
  96. WHAT TYPE OF LINKAGE?
  97. WHY IS LACTOSE A REDUCING SUGAR?
    BECAUSE IT HAS THE ANOMERIC CARBON THAT CAN INTERACT WITH OTHERS. THE -OH GROUP THAT DETERMINES IF IT'S ALPHA OR BETA.
  98. T OR F?
    WHEN UTILIZING DISACCHARIDE NOMACLATURE, STRUCTURAL IDENTIFICATION AND BOND LINKAGE IDENTIFICATION ARE DONE TWO DIFFERENT/OPPOSITE WAYS.
    TRUE
  99. THE alpha(1,4) linkage between two molecules of glucose...DEFINE THE LINKAGE TYPE
    GLYCOSIDIC (OR ACETAL) LINKAGE
  100. -------- is an intermediate product of starch hydrolysis.
    Does not exist freely in nature but readily found in junk food
    • Maltose
    • (malt sugar)
  101. WHAT THE HELL IS THIS?
  102. One molecule of galactose linked to one molecule of glucose FORMS WHAT?
    LACTOSE
  103. two molecules of glucose LINKED TOGTHER FORM WHAT?
    MALTOSE (MALT SUGAR)
  104. --------- is a degradation product of cellulose (i.e. wood and paper) is composed of two molecules of glucose linked with a b(1,4) glycosidic bond
    Do not confuse with lactose!!!!
    • Cellobiose.
    • MUST RECGONIZE FOR TEST!!!!
  105. DEFINE THE ENTITE STRUCTURE AND THE 2 SUBUNITS. MUST KNOW FOR TEST!!
    • Cellobiose is composed of two molecules of glucose linked with a b(1,4) glycosidic bond.
  106. MUST KNOW THIS STRUCTURE:
    • Sucrose is common table sugar (cane or beet
    • sugar) produced in the leaves and stems of plants.

    One molecule of glucose linked to one molecule of fructose, linked by an a,b(1,2) glycosidic bond.

    Glycosidic bond occurs between both anomeric carbons.

    Nonreducing sugar... Both anomeric carbons in bond.
  107. One molecule of glucose linked to one molecule of fructose, linked by an a,b(1,2) glycosidic bond...WHAT AM I?
    • SUCROSE. MUST KNOW FOR TEST!!
  108. WHY IS LINKAGE NAMED DIFFERENTLY ON SUCROSE?
    BECAUSE BOTH ANOMERIC CARBONS ARE LINKED.
  109. DEFINE UNIT, SUBUNITS AND NUMBER CARBONS.
  110. Polysaccharides can be ---- OR ------.
    linear or branched
  111. Polysaccharides have been divided into two classes. NAME THEM
    homoglycans and heteroglycans
  112. DEFINE HOMOGLYCAN POLYSACCHARIDES
    • Have one type of monosaccharide and found in starch, glycogen, cellulose, and chitin.
    • Starch and glycogen are energy storage molecules while chitin and cellulose are structural—
  113. WHAT 2 POLYSACCHARIDES WOULD YOU FIND IN FISH WRAPED IN PAPER?
    CHITIN (FISH) & CELLULOSE (PAPER)
  114. energy reservoir of plant cells and a significant source of carbohydrate in the
    human diet
    STARCH
  115. Two polysaccharides occur together in starch. NAME THEM
    AMYLOSE & AMYLOPECTIN
  116. ----------- is composed of long, unbranched
    chains of D-glucose with a(1,4) linkages between them.
    Amylose
  117. ------------- typically contains thousands of glucose monomers and a molecular weight from
    150,000-600,000 D
    Amylose
  118. ----------- are branched polymer containing both a(1,6) and a(1,4) linkages. Branch points occur every 20 to 25 residues
    amylopectin
  119. In amylopectin, branch point every 20-25 residue on WHAT position?
    SIX

  120. --------is the carbohydrate storage molecule in vertebrates found in greatest abundance in
    the liver and muscle cells
    Up to 8–10% of the wet weight of liver cells and 2–3% in muscle cells
    Glycogen (“starch-like”)
  121. GLYCOGEN VS AMYLOPECTIN...WHAT HAS MORE BRANCH POINTS?
    GLYCOGEN
  122. More compact and easily mobilized than other polysaccharides—used for quick “energy
    source” in the human body but can be depleted rapidly...WHAT IS IT?
    GLYCOGEN
  123. -------- is a polymer of D-glucopyranosides
    linked by BETA (1,4) glycosidic bonds.
    • Cellulose.
    • IT'S A BRUNCH OF CELLOBIOSE BONDED TOGTHER VIA B(1,4) GLYCOSIDIC BONDS. AND CELLOBIOSE IS JUST 2 GLUCOSE.
  124. Pairs of unbranched cellulose molecules (----- glucose units each) are held together by------
    bonding to form sheetlike strips, or --------.
    • 12,000
    • hydrogen
    • microfibrils
  125. Major types: N- and O-linked glycosaminoglycans (glycans), glycan components of glycolipids, and GPI (glycosylphosphatidylinositol)
    anchors...HOMOGLYCAN OR HETEROGLYCAN?
    • Heteroglycans
    • High molecular weight carbohydrate polymers that contain more than one type of monosaccharide
  126. Found on bacteria, virus can be used to attach to host cells.
    LECTINS
  127. Binding of virus and bacteria to cells (lungs, etc.) -------- are proteins that recognize unique carbohydrate sequences on cells.
    Lectins
  128. DEFINE Oligosaccharide
    An oligosaccharide (from the Greek oligos, a few, and sacchar, sugar) is a saccharide polymer containing a small number (typically two to ten[1]) of component sugars, also known as simple sugars (monosaccharides).

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