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Carbohydrates Notes
Carbohydrates Notes
Carbohydrates Notes
GROUP
5. CARBOHYDRATES
ALDOSE KETOSE
INTRODUCTION
Contains an aldehyde group. Contains a ketone group.
- Hydrate (H2o) of carbon (C). Example: Glyceraldehyde Example: Dihydroxyacetone
- Formula:
o CₙH₂ₙOₙ
o Cₙ(H₂O)ₙ
- Refers to the following:
o Polyhydroxy aldehydes
o Polyhydroxy ketones
o Compounds that can be hydrolyzed to
them.
L-Glyceraldehyde (uncommon)
- Haworth Projection
o Used when the structure is in RING
FORM/CYCLIC.
o Enclosed figure.
CARBS PROJECTION: FISCHER
- Numbering: The most oxidized end of the
molecule has the lowest number.
o Many (>1) oxygen.
o Has double bond (=).
D-KETOSES (FISCHER PROJECTION)
Epimer
- 2 sugars that differ in configuration around 1
specific carbon atom.
STEREOISOMERS
- (You’ll observe kung saang carbon nagkaron ng
pag-flip or nagbaligtad yung position ng
hydrogen at hydroxyl group.)
- (D-Galactose: An EPIMER of D-Glucose at C4.)
o CONSEQ: From the structure of glucose
alone, you can generate the structure
of galactose.)
Anomer
- Hemiacetals or hemiketals which differ only in
configuration at carbon-1 which is the
asymmetric (chiral) center.
o (Hemiacetals: from aldehyde)
o (Hemiketals: from ketone)
o (C1: Anomeric Carbon)
- Its asymmetry is a consequence of
mutarotation.
- (Enclosed figure)
CARBOHYDRATES: CONFORMATION
- Designation of Conformations:
o Six-membered ring:
C-chair (stable)
B-boat (unstable)
S-skew or Twist boat - (Presence of brick-red precipitate: Test was
o Five-membered ring: positive; carbs do contain an aldose.)
E-envelope (stable) - (Benedict’s: Uses citrate as a reagent)
T-twist - (Fehling’s: Copper (II) Oxide)
MONOSACCHARIDES: REACTIONS
- Oxidation
- Reduction
- Formation of Derivatives - (CH2OH > -COOH - carboxylic)
o Glycoside Formation
o Exhaustive Methylation
- (Product: Glycoside (O-CH2-CH3) from ethanol
will be added to the position of hydroxyl group
on the reactant side, replacing the H atom.)
- (If Tollen’s, Benedict’s, and Fehling’s reagents
were used > NEGATIVE)
o Why? Because they react only with C1.
MONOSACCHARIDES: AMINO SUGAR FORMATION
- Product: Amino sugar (NH2)
- Most monosaccharide can acquire an amino
group at C2.
- The acquired amino group can be acetylated to
form N-acetyl derivatives.
- (Reagent: Nitric Acid)
- (CHO and CH2OH > COOH – carboxylic acid)
COMPARING USING GLUCOSE
MONOSACCHARIDES: REDUCTION
- Reagent: NaBH₄
o (Sodium borohydride)
- Product: Sugar alcohol (Alditol)
o 1° alcohol
SUGAR SUGAR ALCOHOL - (Maglalagay ng phosphate group.)
Glucose Sorbitol - (H atom was replaced by a phosphate group at
Galactose Galactitol C6)
Mannose Mannitol FORMATION OF DERIVATIVES: FORMATION OF SUGAR
SULFATES
- (REDUCTION:) - Some polysaccharides contain sulfates
o Increase H atoms. esterified at C2, C4 and/or C6.
o Concerns C1 only. - KS: Found especially in the cornea, cartilage,
CHO > CH2OH and bone
CHEMICAL PROPERTIES: FORMATION OF DERIVATIVES - DS: Found mostly in skin, but also in blood
vessels, heart valves, tendons, and lungs.
- Glycoside Formation
- Formation of Amino Sugars
- Formation of Sugar Sulfates
MONOSACCHARIDES: GLYCOSIDE FORMATION
- Substrate: Monosaccharide (hemiacetal)
- Reagent: Alcohol in acid solution
o (HO-CH2-CH3: Ethanol)
- Product: Glycoside (acetal)
o Do not undergo mutarotation.
- Does not react with any of the following:
o Tollen’s
o Benedict’s
o Fehling’s
FORMATION OF DERIVATIVES: FORMATION OF SUGAR - (CONSEQUENCE: Paggamit ng hydroxyl group
SULFATES (cont.) to form glycosidic bond; wala nang H atom = it
becomes the NONREDUCING END)
- The sulfate group is negatively charged at o WHY? Kasi hindi na pwedeng
physiological pH. makapagreact ang O atom sa iba pang
- C4S: An important structural component of incoming na sugar; Nonreactive na siya
cartilage and provides much of its resistance to – may glycosidic bond na kasi, gamit na
compression. - (Reducing end: Buo pa yung hydroxyl group;
pwede pang makapagform ng glycosidic bond;
pwede pang mag-undergo ng reaction.)
- (GLC: Glucose; Pyranosyl: has 6-membered
ring)
DISACCHARIDES: OVERVIEW
- Maltose
- Cellobiose
- Lactose
- Sucrose
DISACCHARIDES: FORMATION
POLYSACCHARIDES: HEPARIN
- Heteropolysaccharide
- Identity of monosaccharide repeating unit:
- Homopolysaccharide o D-glucuronate-2-sulfate
- Identity of monosaccharide repeating unit: N- o N-sulfo-D-glucosamine-6-sulfate
acetyl-α-D-glucosamine - Glycosidic linkage: α(1→4)
- Glycosidic linkage: β(1→4)
- Structure: Linear