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Glyceraldehyde

 

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Glyceraldehyde



 
 
Glyceraldehyde is a triose
Triose

A triose is a monosaccharide containing three carbon atoms. There are only two trioses, an aldotriose and a ketotriose . Trioses are important in Cellular respiration....
 monosaccharide
Monosaccharide

Monosaccharides are the most basic unit of carbohydrates. They are the simplest form of sugar and are usually colorless, water-soluble, crystal solids....
 with chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
3H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
6O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
3. It is the simplest of all common aldose
Aldose

An aldose is a monosaccharide containing one aldehyde group per molecule and having a chemical formula of the form Cnn....
s. It is a sweet colorless crystal
Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
line solid
Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
 that is an intermediate compound in carbohydrate
Carbohydrate

Carbohydrates or saccharides are the most abundant of the four major classes of biomolecules. They fill numerous roles in living things, such as the storage and transport of energy and structural components ....
 metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
. The word comes from combining glycerine and aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
, as glyceraldehyde is merely glycerine with one hydroxide
Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
 changed to an aldehyde.

Glyceraldehyde has a chiral
Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
 center and therefore exists as two different enantiomer
Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are Superpose complete mirror images of each other, much as one's left and right Chirality are "the same" but opposite....
s with opposite optical rotation:





While the optical rotation
Optical rotation

Optical rotation is the rotation of Linear polarization light as it travels through certain materials. It occurs in solutions of chirality molecules such as sucrose , solids with rotated crystal planes such as quartz, and Spin polarization gases of atoms or molecules....
 of glyceraldehyde is (+) for R and (-) for S, this is not true for all monosaccharides.






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Encyclopedia


Glyceraldehyde is a triose
Triose

A triose is a monosaccharide containing three carbon atoms. There are only two trioses, an aldotriose and a ketotriose . Trioses are important in Cellular respiration....
 monosaccharide
Monosaccharide

Monosaccharides are the most basic unit of carbohydrates. They are the simplest form of sugar and are usually colorless, water-soluble, crystal solids....
 with chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
3H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
6O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
3. It is the simplest of all common aldose
Aldose

An aldose is a monosaccharide containing one aldehyde group per molecule and having a chemical formula of the form Cnn....
s. It is a sweet colorless crystal
Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
line solid
Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
 that is an intermediate compound in carbohydrate
Carbohydrate

Carbohydrates or saccharides are the most abundant of the four major classes of biomolecules. They fill numerous roles in living things, such as the storage and transport of energy and structural components ....
 metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
. The word comes from combining glycerine and aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
, as glyceraldehyde is merely glycerine with one hydroxide
Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
 changed to an aldehyde.

Glyceraldehyde has a chiral
Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
 center and therefore exists as two different enantiomer
Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are Superpose complete mirror images of each other, much as one's left and right Chirality are "the same" but opposite....
s with opposite optical rotation:

  • R from Latin rectus meaning right, or
  • S from Latin sinister meaning left


Name of enantiomer
Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are Superpose complete mirror images of each other, much as one's left and right Chirality are "the same" but opposite....
D-glyceraldehyde
(R)-glyceraldehyde
(+)-glyceraldehyde
L-glyceraldehyde
(S)-glyceraldehyde
(-)-glyceraldehyde
Fischer projection
Fischer projection

The Fischer projection, devised by Hermann Emil Fischer in 1891, is a two-dimensional representation of a Three-dimensional space organic molecule by projection....
Skeletal formula
Skeletal formula

The skeletal formula of an organic compound is a shorthand representation of its molecular geometry. Skeletal formulae are ubiquitous in organic chemistry because they show complicated structures clearly and they are quick and simple to draw....
Ball-and-stick model
Molecular model

A molecular model, in this article, is a physical model that represents molecules and their processes. The creation of mathematical models of molecular properties and behaviour is molecular modelling, and their graphical depiction is molecular graphics, but these topics are closely linked and each uses techniques from the others....


While the optical rotation
Optical rotation

Optical rotation is the rotation of Linear polarization light as it travels through certain materials. It occurs in solutions of chirality molecules such as sucrose , solids with rotated crystal planes such as quartz, and Spin polarization gases of atoms or molecules....
 of glyceraldehyde is (+) for R and (-) for S, this is not true for all monosaccharides. The stereochemical rotation can only be determined by the chemical structure, whereas the optical rotation can only be determined empirically (by experiment).

Glyceraldehyde is used as the configurational standard for carbohydrates. Monosaccharides with an identical conformation at the last stereocentre, for example, C5 for glucose
Glucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
, to (R)-glyceraldehyde are assigned the stereo-descriptor D, those similar to (S)-glyceraldehyde are assigned a L. Both, D and L, should be small capital letters
Small caps

In typography, small capitals are uppercase graphemes set at the same height as surrounding lowercase letters or text figures. They are used in running text to prevent capitalized words from appearing too large on the page, and as a method of emphasis or distinctiveness for text alongside or instead of italics, or when boldface is inappr...
.

Glyceraldehyde can be prepared, along with dihydroxyacetone
Dihydroxyacetone

Dihydroxyacetone is a simple carbohydrate that is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin....
, by the mild oxidation of glycerol
Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
, for example with hydrogen peroxide
Hydrogen peroxide

Hydrogen peroxide is a very pale blue liquid which appears colorless in a dilute solution, slightly more viscous than water. It is a weak acid....
 and a ferrous
Ferrous

Ferrous, in chemical science, indicates a bivalent iron compound , as opposed to ferric, which indicates a trivalent iron compound .Outside of chemical science, ferrous is an adjective used to indicate the presence of iron....
 salt
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
 as catalyst.

It was by a lucky guess that the D molecular geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by x-ray crystallography
X-ray crystallography

X-ray crystallography is a method of determining the arrangement of atoms within a crystal, in which a beam of X-rays strikes a crystal and scatters into many different directions....
 in 1951.

See also

  • Stereoisomerism
    Stereoisomerism

    Stereoisomers are isomer that have the same molecular formula and sequence of bonded atoms , but which differ in the three dimensional orientations of their atoms in space....


Further reading

  • On the Assignment of Anomeric Configuration (pdf)