Biomaterial Database

Reactions of polyfunctional amino acids with N,N'-carbonyldiimidazole in aqueous solution--oligopeptide formation. 1977

K W Ehler, and E Girard, and L E Orgel

1. Serine reacts with N,N'-carbonyldiimidazole in aqueous solution at 0 degrees C to yield Nalpha-[imidazolyl-(1)-carbonyl]-L-serine. This compound slowly transforms to L-2-oxo-oxazolidine-5-carboxylic acid. We found that L-2-oxo-oxazolidine-5-carboxylic acid was stable to hydrolysis under a variety of conditions and did not oligomerize to yield peptides. Threonine was found to react in an analogous manner with N,N'-carbonyldiimidazole, yielding Nalpha-[imidazolyl-(1)-carbonyl]-L-threonine and L-(+)-trans-5-methyl-2-oxo-oxazolidine-5-carboxylic acid. 2. Histidine reacts with N,N'-carbonyldimidazole in aqueous solution at 0 degrees C to yield a variety of histidine-containing intermidiates. These slowly transform to give 7-carboxy-imidazole-[1,5cotetrahydropyrimidin-5-one in up to 90% yield. 3. The polymerization of 7-carboxy-imidazo-[1,5c]-tetrahydropyrimidin-5-one in imidazole buffer at 30 degrees gives excellent yields of oligohistidines.

UI	MeSH Term	Description	Entries
D007093	Imidazoles	Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D007202	Indicators and Reagents	Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)	Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D009842	Oligopeptides	Peptides composed of between two and twelve amino acids.	Oligopeptide
D004151	Dipeptides	Peptides composed of two amino acid units.	Dipeptide
D004590	Electrophoresis, Paper	Electrophoresis in which paper is used as the diffusion medium. This technique is confined almost entirely to separations of small molecules such as amino acids, peptides, and nucleotides, and relatively high voltages are nearly always used.	Paper Electrophoresis
D006639	Histidine	An essential amino acid that is required for the production of HISTAMINE.	Histidine, L-isomer,L-Histidine,Histidine, L isomer,L-isomer Histidine
D000596	Amino Acids	Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins.	Amino Acid,Acid, Amino,Acids, Amino
D012694	Serine	A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.	L-Serine,L Serine
D013912	Threonine	An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.	L-Threonine,L Threonine