Biomaterial Database

The glycerol teichoic acid of walls of Staphylococcus lactis I3. 1968

A R Archibald, and J Baddiley, and D Button

1. The teichoic acid from walls of Staphylococcus lactis I3 was isolated by extraction with trichloroacetic acid and shown to contain glycerol, N-acetylglucosamine, phosphate and d-alanine in the molecular proportions 1:1:2:1. The alanine is attached to the polymer through ester linkages. 2. Hydrolysis with acid gave alanine, glucosamine and glycerol diphosphates. Under mild acid conditions a repeating unit was produced; this consists of glycerol diphosphate joined through a phosphodiester group to N-acetylglucosamine. 3. Hydrolysis with alkali gave glycerol diphosphates, saccharinic acid and two phosphodiesters containing glucosamine whose structures were elucidated; these both contain glucosamine 1-phosphate, and N-acetylglucosamine 1-phosphate was isolated by a degradative procedure. 4. The unusual properties of the teichoic acid are explained by a polymeric structure in which N-acetylglucosamine 1-phosphate is attached through its phosphate to glycerol phosphate. 5. The biosynthetic implications of this structure are discussed.

UI	MeSH Term	Description	Entries
D010428	Pentosephosphates
D010710	Phosphates	Inorganic salts of phosphoric acid.	Inorganic Phosphate,Phosphates, Inorganic,Inorganic Phosphates,Orthophosphate,Phosphate,Phosphate, Inorganic
D011135	Polysaccharides, Bacterial	Polysaccharides found in bacteria and in capsules thereof.	Bacterial Polysaccharides
D002473	Cell Wall	The outermost layer of a cell in most PLANTS; BACTERIA; FUNGI; and ALGAE. The cell wall is usually a rigid structure that lies external to the CELL MEMBRANE, and provides a protective barrier against physical or chemical agents.	Cell Walls,Wall, Cell,Walls, Cell
D004952	Esters	Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water.	Ester
D005944	Glucosamine		2-Amino-2-Deoxyglucose,Dona,Dona S,Glucosamine Sulfate,Hespercorbin,Xicil,2 Amino 2 Deoxyglucose,Sulfate, Glucosamine
D005990	Glycerol	A trihydroxy sugar alcohol that is an intermediate in carbohydrate and lipid metabolism. It is used as a solvent, emollient, pharmaceutical agent, or sweetening agent.	1,2,3-Propanetriol,Glycerin,1,2,3-Trihydroxypropane,Glycerine
D000143	Acids	Chemical compounds which yield hydrogen ions or protons when dissolved in water, whose hydrogen can be replaced by metals or basic radicals, or which react with bases to form salts and water (neutralization). An extension of the term includes substances dissolved in media other than water. (Grant & Hackh's Chemical Dictionary, 5th ed)	Acid
D000409	Alanine	A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.	Abufène,Alanine, L-Isomer,L-Alanine,Alanine, L Isomer,L Alanine,L-Isomer Alanine
D000468	Alkalies	Usually a hydroxide of lithium, sodium, potassium, rubidium or cesium, but also the carbonates of these metals, ammonia, and the amines. (Grant & Hackh's Chemical Dictionary, 5th ed)	Alkali,Alkalis