Carbohydrates and Inositols

Carbohydrates are ubiquist in nature and are an important group of naturally ocurring organic compounds. They are especially prevalent in plants where they make up to 80% of the anhydrous mass. Particularly significant are cellulose, starches, pectines and the sugars saccharose and glucose. In mammals glucose is an essential component in blood and in its polymeric form, glycogen, in the liver and in muscles. Carbohydrates are found in adenintriphosphat, a key substance in the biological energy storage and the energy transport as well as in the nucleic acid, being responsible for the storage and the transfer of the genetic code and the control of the production of proteins. However, carbohydrates are also part of a wide variety of extensively presribed pharmaceuticals, for example bear many antibiotics at least one or two sugar moieties. The name carbohydrates is derived of their structure which usually conists of the general chemical formula Cx(H2O)y or its derivatives. However, some prominent exeptions to this rule include the important carbohydrates deoxyribose and glycerol, although they cannot be considered as carbohydrates in a strict sense. Often, derivatives containing other heteroatoms than oxygen are equally counted as carbohydrates. The classification of carbohydrates is usually based on their number of sugar units into monosaccharides, disaccharides, oligosaccharides, and polysaccharides.

Monosaccharides
Monosaccharides can be divided into aldoses and ketoses. Aldoses typically possess an aldehyde group on the first carbon atom while ketoses inherit a ketone functionality on the second carbon atom. Another commonly used method classifies carbohydrates according on their number of carbon atoms. Examples are trioses, tetroses, pentoses and hexoses with three, four, five or six carbon atoms in the skeleton. Monosaccharides can either be present in their straight chain structure or, alternatively, a hydroxyl group can react intramolecularly with the aldehyde or ketone functionality to form a hemiacetal or hemiketal. In this case a heterocyclic ring with an oxygen bridge is formed. Rings with five carbon atoms are called furanoses, rings with six carbon atoms are named pyranoses. They both exist in equilibrium with their straight-chain forms. During the formation of the hemiacetal or -ketal the previous aldehyde or ketone carbon atom becomes a new stereocenter. Therefore two diastereomeric cyclic forms are established: the alpha- and the beta-anomers.

D-Glucose

Equilibrium between aldehyde and hemiacetals in D-glucose.


Examples of Biosynth's triose derivatives

Cat. No. - Product Name
D-6000 - 1,2-Dipalmitoyl-rac-glycerol
G-4100 - D-Glyceraldehyde sirop
G-4120 - DL-Glyceraldehyde (Dimer)
G-4140 - L-Glyceraldehyde sirop
G-4190 - beta-Glycerophosphate, disodium salt pentahydrate (max. 10% alpha) culture media grade
G-4200 - beta-Glycerophosphate, disodium salt pentahydrate (max. 2% alpha)

Examples of Biosynth's tetrose derivatives

Cat. No. - Product Name
D-8100 - 1,4-Dithioerythritol (DTE)
D-8200 - 1,4-Dithiothreitol (DTT)
D-8220 - L-1,4-Dithiothreitol (L-DTT)
E-3000 - meso-Erythritol
E-3200 - D-Erythrose

Examples of Biosynth's pentose derivatives

Cat. No. - Product Name
A-3000 - Adonitol
A-8240 - L-Arabinose
D-4160 - 1,2:3,5-Di-O-isopropylidene-alpha-D-xylofuranose
R-5560 - D-Ribose 5-phosphate, barium salt
T-6301 - 1,3,5-Tri-O-benzoyl-alpha-D-ribofuranose
X-7000 - Xylitol

Biosynth's hexose derivatives

Cat. No. - Product Name
B-8975 - 1-Bromo-2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside
D-0460 - 6-Deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranoside
D-0750 - 1,2:3,4-Diacetone-beta-D-glucopyranoside
D-3950 - 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranoside
D-4080 - 2,3:4,6-Di-O-isopropylidene-alpha-L-sorbofuranose
E-8900 - Ethyl-beta-D-thiogalactopyranoside
F-7440 - D-Fructose 1,6-diphosphate, tetrasodium salt
G-8500 - L-Gulono-gamma-lactone
K-2030 - 5-Keto-D-gluconic acid, hemicalcium salt


Biosynth's heptose derivatives.

Cat. No. - Product Name
G-2900 - D-Glucoheptose
G-4170 - D-glycero-D-galacto-Heptose
M-0975 - D-Mannoheptose
M-0980 - D-Mannoheptulose
S-2200 - Sedoheptulose anhydride monohydrate

Biosynth's neuraminic acid derivatives

Cat. No. - Product Name
A-1600 - N-Acetylneuraminic acid
A-1605 - N-Acetylneuraminic acid dihydrate (synthetic)
A-4905 - 9-Amino-N-acetylneuraminic acid
A-9890 - 9-Azido-N-acetylneuraminic acid


Disaccharides

Disaccharides consist of two monosaccharide subunits linked together by a covalent glycosidic bond. During the addition reaction of the two sugars water is released. The most common disaccharides include sucrose (one glucose and one fructose subunit), lactose (one glucose and one galactose subunit) and maltose (two glucose subunits). Under mildly acid conditions disaccharides are hydrolyzed into two equivalents of the corresponding monosaccharides.

Oligo- and Polysaccharides

Oligo- and polysaccharides consist of several monosaccharide subunits linked together via glycosidic bonds. While oligosaccharides are defined as composed of three to ten sugars, polysaccharides contain more than ten monosaccharide units. Oligosaccharides play an important role in the protein posttranslational modification. Polysaccharides serve as versatile biological polymers. Prominent examples include starch, cellulose and chitin.

Examples of Biosynth's di-, oligo- and polysaccharides

Cat. No. - Product Name
H-1722 - 2,2',3,3',4',6,6'-Hepta-O-acetyl-D-cellobiose
H-3450 - Hyaluronic acid, sodium salt
M-0945 - beta-D-Maltose octaacetate
R-1000 - D-Raffinose pentahydrate



Inositols

Inositol, a sugar-like molecule, was discovered in the 19th century. Although much of its chemistry had been disclosed by the beginning of the 20th century, it was only in the 1980s and 90s that the huge number of inositol-containing molecules, also called inositides, and their important functions, especially in intracellular signalling, has become evident. Molecules bearing an inositol part can be distinguished into two categories: Inositol lipids and inositol phosphates. While former are hydrophobic and form part of the structure of cell membranes, the latter are soluble in aqueous solutions and found primarily in the cytoplasm. However, the functions of inositol derivatives are as many-sided as their structures. For example inositol 1,4,5-triphosphate plays a key role in the rapid response of tissues to hormones and inositol 3,4,5,6 tetrakisphosphate is considered to be a crucial regulator of chloride channels in epithelia. (please click here for more information about insitols)

Examples of Biosynth's inositol derivatives:
Cat. No. - Product Name
B-0703 - 6-O-Benzyl-2,3:4,5-di-O-cyclohexylidene-L-myo-inositol
B-0720 - 1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-myo-inositol
D-7950 - 1,6:3,4-Di-O-(tetraisopropyl-1,3-disiloxanediyl)-)-myo-inositol
I-6500 - myo-Inositol
I-7970 - 1,2-O-Isopropylidene-myo-inositol
I-7974 - 1,2-O-Isopropylidene-3,4,5,6-tetra-O-benzoyl-myo-inositol

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