Biomaterial Database

Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea. 1984

K W Stahl, and F E Köster

The axial (ax.) and equatorial (eq.) diastereomeric forms of phosphate triesters resulting from reactions of N-ethyl, N-nitrosourea with 3 cyclic mononucleotides were analyzed by column liquid chromatography (CLC). Evidence is presented that the 2'OH group of 3', 5'cAMP essentially contributes to the stereoselective eq. alkyl substitution, most probably by hydrogen bonding catalysis. The neighboring group direction of ethylation gives substantial support to non-random DNA alkylations by NEU.

UI	MeSH Term	Description	Entries
D008956	Models, Chemical	Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment.	Chemical Models,Chemical Model,Model, Chemical
D009607	Nitrosourea Compounds	A class of compounds in which the core molecule is R-NO, where R is UREA.	Compounds, Nitrosourea
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D004247	DNA	A deoxyribonucleotide polymer that is the primary genetic material of all cells. Eukaryotic and prokaryotic organisms normally contain DNA in a double-stranded state, yet several important biological processes transiently involve single-stranded regions. DNA, which consists of a polysugar-phosphate backbone possessing projections of purines (adenine and guanine) and pyrimidines (thymine and cytosine), forms a double helix that is held together by hydrogen bonds between these purines and pyrimidines (adenine to thymine and guanine to cytosine).	DNA, Double-Stranded,Deoxyribonucleic Acid,ds-DNA,DNA, Double Stranded,Double-Stranded DNA,ds DNA
D005038	Ethylnitrosourea	A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.	Nitrosoethylurea,N-Ethyl-N-nitrosourea,N Ethyl N nitrosourea
D006860	Hydrogen Bonding	A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds.	Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D000227	Adenine Nucleotides		Adenine Nucleotide,Adenosine Phosphate,Adenosine Phosphates,Nucleotide, Adenine,Nucleotides, Adenine,Phosphate, Adenosine,Phosphates, Adenosine
D000478	Alkylation	The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group.	Alkylations