BIOCHEMISTRY - MD1 (CARBOHYDRATES)

THIS IS DERIVED FROM THE TERM HYDRATE DE CARBONE

CARBOHYDRATES

COMPOUNDS OF CARBOHYDRATES ARE COMPOSED OF?

CARBON, HYDROGEN, OXYGEN

EMPIRICAL FORMULA OF CARBOHYDRATES

(CH2O)N = C5H10O5

THE EMPIRICAL FORMULA OF CARBOHYDRATES ARE ONLY APPLICABLE ON WHAT TYPE OF SUGARS?

SIMPLE SUGARS

TRUE OR FALSE. IN COMPOUND SUGARS, THE MORE CARBON YOU ADD THE MORE YOU TAKE OUT OXYGEN

TRUE

THIS IS THE MOST ABUNDANT COMPOUNDS FOUND IN NATURE

CARBOHYDRATES

THIS IS THE MOST ABUNDANT AMONGST THE SUGAR (HOMOSUGAR); 100 BILLION TONS ANNUALLY

CELLULOSE

THESE HAVE A LARGE NUMBER OF HYDROXYL GROUPS (POLYHYDROXYL)

CARBOHYDRATES

CARBOHYDRATES MAY ALSO CONTAIN WHAT GROUPS?

ALDEHYDE GROUPS (POLYHYDROXYALDEHYDES) AND KETO GROUPS (POLYHYDROXYKETONES)

THIS IS A HYDROGEN CONNECTED TO A CARBON, AND A CARBON CONNECTED BY A DOUBLE BOND TO AN OXYGEN

ALDOSES

A KETONE GROUP WITHOUT THE HYDROGEN

KETOSE

THE DERIVATIVES OF CARBOHYDRATES MAY ALSO CONTAIN ____

NITROGEN, PHOSPHORUS, SULFUR

CARBOHYDRATES CAN BE PRODUCED BY PLANTS VIA?

PHOTOSYNTHESIS

FUNCTION OF ___ IS FOR PRIMARY/IMMEDIATE SOURCES OF ENERGY, ESPECIALLY FOR BRAIN CELLS (85-90%) AND RBCS (MATURE RBCS BECAUSE THEY DO NOT HAVE MITOCHONDRIA)

CARBOHYDRATES

SIMPLE SUGARS (TRIOSIS, TETROSES, PENTOSES, HEXOSES)

MONOSACCHARIDES (MONOSES, GLYCOSES, MONOSUGARS)

CLASSIFICATION OF CARBOHYDRATES (DI, TRI, TETRA, PENTA, UP TO 9 OR 10)

OLIGOSACCHARIDES

IN OLIGOSACCHARIDES, THE MOST IMPORTANT ARE THE?

DISACCHARIDES (SUCROSE, LACTOSE, MALTOSE)

ONE TYPE OF SUGAR

HOMOPOLYSACCHARIDES

TWO OR MORE TYPES OF SUGAR

HETEROPOLYSACCHARIDES

THIS IS ALSO KNOWN AS SIMPLE SUGARS

MONOSACCHARIDES

THIS IS CLASSIFIED EITHER BY THE NUMBER OF CARBON ATOM OR BY THE NATURE OF FUNCTIONAL GROUP—ALDOSES OR KETOSES

MONOSACCHARIDES

MOST OF THE CARBOHYDRATES (99%) ARE STRAIGHT CHAIN COMPOUNDS

MONOSACCHARIDES

THIS IS THE SIMPLEST OF THE ALDOSES (ALDOTRIOSE)

D-GLYCERALDEHYDE

PARENT COMPOUND OF THE ALDOSES (3C)

D-GLYCERALDEHYDE

THIS IS THE SIMPLEST KETOSE (KETOTRIOSE)

DIHYDROXYACETONE (DHA)

PARENT COMPOUND OF THE KETOSE (3C)

DIHYDROXYACETONE (DHA)

THIS CANNOT BE HYDROLYZED INTO SIMPLER CARBOHYDRATES

MONOSACCHARIDES

THIS IS THE MOST IMPORTANT MONOSACCHARIDE

GLUCOSE

NATURALLY OCCURRING MONOSACCHARIDES HAVE HOW MANY CARBON ATOMS?

3 TO 7

WHAT IS THE MOST COMMONLY USED CARBON SPECIES FOR NATURALLY OCCURING MONOSACCHARIDES?

5 AND 6

THESE ARE WATER SOLUBLE, WHITE, CRYSTALLINE SOLIDS

PURE MONOSACCHARIDES

GLUCOSE IS AN EXAMPLE OF A:

A. POLYHYDROXY ALDEHYDE

B. POLYHYDROXY KETONE

A

FRUCTOSE IS AN EXAMPLE OF A:

A. POLYHYDROXY ALDEHYDE

B. POLYHYDROXY KETONE

B

THIS IS A CARBON ATOM TO WHICH 4 DIFFERENT GROUPS ARE ATTACHED

ASYMMETRICAL/CHIRAL CARBON

ALL MONOSACCHARIDES HAVE CHIRAL CARBON EXCEPT FOR?

DIHYDROXYACETONE (DHA)

TRUE OR FALSE. DIFFERENT ISOMERS ARE POSSIBLE BASED ON THE PRESENCE OF ASYMMETRICAL/CHIRAL CARBON ATOMS

TRUE

HOW MANY POSSIBLE ISOMERS CAN ALDOTRIOSE HAVE?

2

HOW MANY POSSIBLE ISOMERS CAN ALDOTETROSE HAVE?

4

THIS IS A KETOSE THAT DOES NOT HAVE A CHIRAL CARBON

DIHYDROXYACETONE

THE DESIGNATION OF A SUGAR ISOMER AS THE D FORM OR OF ITS MIRROR IMAGE AS THE L FORM IS DETERMINED BY COMPARISON OF ITS SPATIAL RELATIONSHIP TO THE PARENT COMPOUND OF THE CARBOHYDRATES WHICH IS THE?

THREE CARBON SUGAR GLYCEROSE (GLYCERALDEHYDE)

THE THREE CARBON SUGAR GLYCEROSE (GLYCERALDEHYDE) IS ALSO CALLED THE ___ IN THE DETERMINATION OF D AND L ISOMERISM

REFERENCE SUGAR

TRUE OR FALSE. THE ORIENTATION OF THE -H AND -OH GROUPS AROUND THE CARBON ADJACENT TO THE TERMINAL PRIMARY ALCOHOL CARBON DETERMINES WHETHER IT IS D OR L SERIES

TRUE

MOST OF THE MONOSACCHARIDES OCCURRING IN MAMMALS ARE ___ AND THE ENZYMES RESPONSIBLE FOR THEIR METABOLISM ARE SPECIFIC FOR THIS CONFIGURATION

D SUGARS

SIMPLE MONOSACCHARIDES WITH FOUR, FIVE, SIX, AND SEVEN CARBON ATOMS HAVE MULTIPLE ASYMMETRIC CARBONS. THEY EXIST AS _____, ISOMERS THAT ARE NOT MIRROR IMAGES OF EACH

DIASTEREOMERS

THESE ARE STEREOISOMERS WHOLE MOLECULES ARE NONSUPERIMPOSABLE MIRROR IMAGES OF EACH OTHER

ENANTIOMERS

AN ENANTIOMER WITH CHIRAL CENTER AND OH GROUP IS ON THE RIGHT

D ISOMER

ENANTIOMER WITH CHIRAL CENTER AND OH GROUP IS ON THE LEFT

L ISOMER

THE CARBON CHAIN IS NUMBERED STARTING AT THE?

CARBONYL GROUP

THIS IS USED TO DETERMINE D OR L CONFIGURATION

THE HIGHEST NUMBERED CHIRAL CENTER

THIS IS WHEN A BEAM OF PLANE-POLARIZED LIGHT IS PASSED THROUGH A SOLUTION OF AN OPTICAL ISOMER

OPTICAL ISOMERISM

IN OPTICAL ISOMERISM, IF IT ROTATES TO THE RIGHT, THEN THIS IS ____

DEXTROROTATORY (+)

IN OPTICAL ISOMERISM, IF IT ROTATES TO THE LEFT, THEN THIS IS ____

LEVOROTATORY (-)

DEXTROSE IS ___ BECAUSE IT TURNS TO THE RIGHT IN OPTICAL ISOMERISM

DEXTROROTATORY

TRUE OR FALSE. THE DIRECTION OF ROTATION OF POLARIZED LIGHT IS DEPENDENT ON THE STEREOCHEMISTRY OF THE SUGAR

FALSE (INDEPENDENT)

THIS IS THE MEASUREMENT OF OPTICAL ACTIVITY IN CHIRAL OR ASYMMETRIC MOLECULES USING POLARIZED LIGHT

POLARIMETRY

THESE ARE THE MIDDLE ASYMMETRIC CARBONS OTHER THAN THE SUB TERMINAL ONE

EPIMERS

ISOMERS DIFFERING AS A RESULT OF VARIATION IN CONFIGURATION OF THE OH AND H CARBON ATOMS 2, 3, 4 OF GLUCOSE ARE KNOWN AS?

EPIMERS

THE MOST IMPORTANT EPIMERS OF GLUCOSE ARE?

MANNOSE AND GALACTOSE

MANNOSE IS AN EPIMER OF GLUCOSE LOCATED AT WHAT CARBON?

CARBON 2

GALACTOSE IS AN EPIMER OF GLUCOSE LOCATED AT WHAT CARBON?

CARBON 4

TRUE OR FALSE. MANNOSE AND GALACTOSE ARE EPIMERS OF EACH OTHER AS THEY DIFFER IN CONFIGURATION ON THE SAME CARBON

FALSE

THE RING STRUCTURE OF AN ALDOSE IS?

HEMIACETAL

THIS IS FORMED BY THE COMBINATION OF AN ALDEHYDE AND

TO FORM HEMIACETAL, THERE SHOULD BE A COMBINATION OF THE HYDROXYL GROUP AND THE ALDEHYDE GROUP IN WHICH THE CARBON NUMBERS ARE LOCATED AT?

C1 AND C5

THE RING STRUCTURE OF A KETOSE IS A?

HEMIKETAL

THIS IS FORMED BY THE COMBINATION OF A KETONE AND AN ALCOHOL GROUP

HEMIKETAL

TO FORM HEMIKETAL, THERE SHOULD BE A COMBINATION OF THE HYDROXYL GROUP AND THE KETONE GROUP IN WHICH THE CARBON NUMBERS ARE LOCATED AT?

C2 AND C5

THE RING CAN OPEN AND RECLOSE ALLOWING THE ROTATION TO OCCUR AROUND THE CARBON BEARING REACTIVE CARBONYL GROUP YIELDING TO 2 POSSIBLE CONFIGURATIIONS WHICH ARE?

ALPHA AND BETA FORM OF HEMIACETAL AND HEMIKETAL

THIS IS THE CARBON ABOUT WHICH ROTATION OCCURS. THIS IS ALSO THE CARBOXYL GROUP BEFORE THE SUGAR TRANSFORMED INTO A RING FORM

ANOMERIC CARBON

HYDROXYL ATTACHED TO THE ANOMERIC CARBON OF THE RIGHT RING

ALPHA CONFIGURATION

HYDROXYL ATTACHED TO THE ANOMERIC CARBON OF THE LEFT RING

BETA CONFIGURATION

WHEN RING STRUCTURE IS FORMED, THE HYDROXYL OF THIS CONFIGURATION IS PLACED DOWNWARDS

ALPHA CONFIGURATION

WHEN RING STRUCTURE IS FORMED, THE HYDROXYL OF THIS CONFIGURATION IS PLACED UPWARDS

BETA CONFIGURATION

THIS IS THE SPONTANEOUS CHANGE BETWEEN THE ALPHA AND BETA CONFIGURATION THROUGH THE FORMATION OF INTERMEDIATE OPEN CHAIN

MUTAROTATION

THIS IS THE GRADUAL CHANGE OF SPECIFIC OPTICAL ROTATION OF SUGAR

MUTAROTATION

WHAT IS AN EXMPLE OF ALDOSE-KETOSE ISOMERS?

GLUCOSE AND FRUCTOSE

WHAT ARE THE STRUCTURAL REPRESENTATION OF SUGARS?

FISCHER PROJECTION, HAWORTH PROJECTION, CHAIR AND BOAT CONFORMATIONS

WHAT ARE THE REACTIONS OF MONOSACCHARIDES?

OSAZONE FORMATION, REDUCTION, OXIDATION, ACTION OF ALKALI, ACTION OF ACID, GLYCOSIDE FORMATION, ESTER FORMATION

REACTION OF MONOSACCHARIDES THAT IS USED FOR THE IDENTIFICATION OF SUGARS

FORMATION OF OSAZONES

IN THE FORMATION OF OSAZONES, THIS CONSISTS OF REACTING THE MONOSACCHARIDE WITH?

PHENYLHYDRAZINE

A CRYSTALLINE COMPOUND WITH A SHARP MELTING POINT AND A CHARACTERISTIC SHAPE IS OBTAINED

FORMATION OF OSAZONES

THIS GIVES THE SAME NEEDLE-SHAPED OSAZONE CRYSTALS AS D-GLUCOSE

D-FRUCTOSE AND D-MANNOSE

TYPE OF REACTION OF MONOSACCHARIDES THAT IS SELDOM USED THESE DAYS FOR IDENTIFICATION

FORMATION OF OSAZONES

THIS IS MORE COMMONLY USED NOWADAYS FOR THE IDENTIFICATION OF SUGARS WHICH IS A BETTER AND MORE EFFICIENT WAY OF IDENTIFYING SUGARS

HPLC OR MASS SPECTROMETRY

ALDOSES MAY BE OXIDIZED TO 3 TYPES OF ACIDS WHICH ARE?

ALDONIC, URONIC, SACCHARIC (GLYCARIC)

THIS IS WHEN ALDEHYDE GROUP IS CONVERTED TO A CARBOXYL GROUP (COOH)

ALDONIC ACIDS

WHAT ARE EXAMPLES OF ALDONIC ACIDS?

GLUCOSE, GALACTOSE, MANNOSE

WHAT IS THE ALDONIC ACID OF GLUCOSE?

GLUCONIC ACID

WHAT IS THE ALDONIC ACID OF GALACTOSE

GALACTONIC

WHAT IS THE ALDONIC ACID OF MANNOSE?

MANNONIC ACID

THIS OXIDATION IS WHEN AN ALDEHYDE GROUP IS LEFT INTACT (IT REMAINS) WHILE THE OTHER ALCOHOL AT THE OTHER END IS OXIDIZED TO A CARBOXYL GROUP (COOH)

URONIC ACIDS

WHAT IS THE URONIC ACID OF GLUCOSE?

GLUCURONIC ACID

WHAT IS THE URONIC ACID OF GALACTOSE

GALACTURONIC ACID

WHAT IS THE URONIC ACID OF MANNOSE

MANNURONIC ACID

THIS IS WHEN THERE IS AN OXIDATION AT BOTH ENDS OF MONOSACCHARIDES

SACCHARIC ACID (GLYCARIC ACID)

WHAT IS THE SACCHARIC ACID OF GLUCOSE?

GLUCO SACCHARIC ACID

WHAT IS THE SACCHARIC ACID OF GALACTOSE?

MUCIC ACID

WHAT IS THE SACCHARIC ACID OF MANNOSE?

MANNARIC ACID

REACTION FOR MONOSACCHARIDES THAT IS EITHER DONE BY CATALYTICALLY OR ENZYMATICALLY

REDUCTION

THE RESULTANT PRODUCT IN REDUCTION REACTION IS?

POLYOL OR SUGAR ALCOHOL