UOT- Chap 24 - CARBOHYDRATES - SUGAR

Haworth projection

A method for depicting cyclic sugars as planar rings with -OH groups sticking up or down from the plane of the sugar

line notation

A notation method describes the anode and cathode of a battery. anode|electrolyte||electrolyte|cathode -make arrow from anode to cathode to show e- transfer -one | is phase boundary (solid vs solution) -two | (||) is physical boundary (two different beakers)

pyranose

A six-membered ring sugar One of two stable cyclic molecules

starch

A storage polysaccharide in plants consisting entirely of glucose.

cellulose

A substance (made of sugars) that is common in the cell walls of many organisms

Anomer

A sugar diastereomer differing only in the position of the hydroxyl at the anomeric carbon - a designated alpha and beta

reducing sugar

A sugar that can reduce other compounds and that readily reduce Tollens's and Fehling's solution - sugars containing hemiacetal function -

fiber

A tough complex carbohydrate that the body cannot digest

alpha anomer

Alpha axial fishes down in the sea, Birds in the air - the anomeric carbon pointing up downward

rendition

An interpretation or translation; a performance

hydrolysis

Breaking down complex molecules by the chemical addition of water

cyanide ion

CN charge -1

Polysaccharide

Carbohydrates that are made up of more than two monosaccharides - constitutes the framework of cellulose and starch

dextrorotatory

Compound that rotates the plane of polarized light to the right, or clockwise (labeled '+')

Trisaccharide

Ether formation between mono- and a disaccharide, eventually produces natural polymer (polysaccharide)

Condensation

Gas to liquid

constitute

To make up; be the parts of

Epimer

Two Diastereomers that differ at only one stereocenter (chiral center).

ribose

a building block of the ribonucleic acids - an aldopentose

glycoside

a cyclic acetal formed by reaction of a monosaccharide with an alcohol, accompanied by loss of H2O

dextrose

a form of glucose found in human blood

fuel

a material that releases energy when it burns

hexagon

a polygon with 6 sides

petagon

a polygon with five sides

sugar

a simple carbohydrate molecule - are polyhydroxy aldehydes and ketones

aldonic acid

a sugar produced by oxidation of an aldose aldehyde group to a carboxylic acid group

alditols

aldehyde groups of sugars are reduced to hydroxyl groups - oxidative cleavage of vicinal diol units, reduction to -----

glucose

also known as dextrose, blood sugar, or grape sugar - Greek, = sweet - is a pentahydroxyhexanal and hence belongs to the class of aldohexose - occurs naturally in many fruits and plants and in conc ranging from 0.08 to 0.1% in human blood.

Di- and higher saccharides

are formed by the combination of hemiacetal and alcohol hydroxy groups of 2 sugars to give an acetal linkage

polyhydroxycarbonyl

are molecules with more than one hydroxyl group (−OH), and a carbonyl group (C=O) either at the terminal carbon atom (aldose) or at the second carbon atom (ketose) are called carbohydrates

diastereomer

are stereoisomers that are not mirror images of one another and are non-superimposable on one another. Stereoisomers with two or more stereocenters can be diastereomers. It is sometimes difficult to determine whether or not two molecules are diastereomers.

complex sugars

are those formed by the linkage of simple sugars through ether bridges

hydrated carbon

because they had the empirical formula CH2O

aldaric acid

both ends of sugars are oxidized - COOH on both ends - double oxidation

aldoses (aldehylic sugar)

carbohydrates containing an aldehyde group *Aldehyde group: H—C =O *CHO at the end of the chain on the first carbon

tetroses

carbohydrates w/ 4 carbons

fibrous

consisting of or characterized by fibers

glucometer

device for measuring blood glucose levels from a drop of blood obtained by a fingerstick

absolute configuration

gives the stereochemistry of a compound without having to compare to other molecules

sucrose

glucose + fructose - the most widely occurring disaccharide in nature - obtained from sugar beet and sugar cane

Ruff chain shortening

in which the low sugars relies on - a terminal carbon being expelled as CO2

chain lengthening

in which the synthesis of high sugars is based on - the new carbon being introduced by cyanide ion

designated

indicated; pointed out

glycosyl group

is a univalent free radical or substituent structure obtained by removing the hemiacetal hydroxyl group from the cyclic form of a monosaccharide and, by extension, of a lower oligosaccharide.

aglycons

is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the -----of a cardiac glycoside would be a steroid molecule.

acetone

ketone that is found in blood, urine, and breath when diabetes mellitus is out of control

nucleic acid

macromolecule containing hydrogen, oxygen, nitrogen, carbon, and phosphorus

polyfunctional

posses multiple functional groups

levorotatory

refers to a substance that rotates the plane of polarized light to the left

horizontal line (in Fischer projection)

represent bond to atoms above the plane of page

scrolled

rolled up

beta anomer

the OH group of the C1 cis to the CH2OH group *it will be equatorial and up* - the anomeric carbon pointing up

acetal linkage

the anomeric sugar carbon is condensed with an alcohol, amine or thiol

inversion of sucrose

the change in optical rotation observed in acidic aqueous solutions of sucrose - is due to the equilibrium of staring sugar with various cyclic and anomeric forms of its component monomers

fructose

the corresponding constitutional isomeric ketohexose of glucose - the sweetest natural sugar ( some synthetic sugars are sweeter) - present in many fruit and in honey - Latin, fructus = fruit

D

the highest-numbered stereocenter is R

L

the highest-numbered stereocenter is S

anomeric carbon

the new chiral center formed in ring closure; it was the carbon containing the carbonyl in the straight-chain form - the new stereocenter formed by cyclization

cyclization

the ring formation of carbohydrates form their straight-chain form

govern

to be in charge of; to control or rule

elucidate

to clarify, explain

obtain

to get or gain through some effort

Acetal Formation

use of acid, water comes off, alcohol attacks

Fischer proof

uses the techniques of chain lengthening and shortening together with the symmetry properties of aldaric acids to determine the structures of the alsoses

ribonucleic acids

RNA

saliva

The fluid released when the mouth waters that plays an important role in both mechanical and chemical digestion

mutarotation

The rapid interconversion between different anomers of a sugar - The measured optical rotation in whicm between equilibrium between anomers in solution give rises to change

Esterification

The reaction of an alcohol with a carboxylic acid to produce an ester and water.

triose

3 carbon sugar

ketose

A carbohydrate whose carbonyl group is a ketone - with a ketone fxn

aldose

A carbohydrate whose carbonyl group is an aldehyde

dehydration synthesis

A chemical reaction in which two molecules covalently bond to each other with the removal of a water molecule.

Disaccharide

A double sugar, consisting of two monosaccharides joined by dehydration synthesis - the formation of ether (usually, acetal) bridge.

furanose

A five-membered ring sugar One of two stable cyclic molecules

hemiacetal

A functional group that contains a carbon atom bonded to one -OR group, one -OH group, an alkyl chain, and a hydrogen atom.

array

A large group of people or things

margin

1,3-dihydroxyacetone - one of 2 simplest members of monosaccharides - is a ketotriose

Monosaccharides (simple sugar)

- is an aldehyde or ketone containing at least 2 addtional hydroxy groups - are called aldoses if they are aldehydes and ketoses if they are ketones.

glyceraldehyde (2,3 dihydroxypropanal)

- the simplest aldose - is an aldotriose - carbonyl carbon is most oxidized, always lowest number - aldehyde carbon can participate in glycosidic linkages

D family

-in which most natural carbohydrates belong to - is the stereocenter farthest from the carbonyl group has the same configuration as that in (R)-(1)-2,3-dihydroxypropanal [d-(1)-glyceraldehyde].