Biomaterial Database

Semi-reversible cross-linking. Synthesis and application of a novel heterobifunctional reagent. 1981

K Friebel, and H Huth, and K D Jany, and W E Trommer

The synthesis of a novel heterobifunctional cross-linking reagent, 3-(4-azido-2-nitrobenzoylseleno)propionic acid is described. The selenol ester function serves as a selective and reversible thiol reagent. Cross-linking is carried out photochemically via nitrene generation. The reagent is well suited for the identification of the environment of a defined cysteine residue according to the principle of semi-reversible cross-linking (Trommer, W.E., Friebel, K., Kiltz, H.-H. & Kolkenbrock. H. (1977) Adv. Exp. Med. Biol. 86A, 187-195). Cleavage of the thiol ester bond (the first anchor point) can be achieved by a variety of labels carrying an amino function thus giving rise to labelled amino acids or proteins in a distance of about 0.7 nm from the known cysteine residue. Optimal conditions were determined by reaction of 3-(4-azido-2-nitrobenzoylseleno)propionic acid and of its unsubstituted analog with glutathione and N alpha-benzoylglycyllysine. Nucleosidetriphosphate-adenylate kinase from pig muscle was chosen as an example to demonstrate the usefulness of the reagent. 14C-labelled aminobutyric acid was applied to cleave the thiol ester bond between the reagent and cysteine-25 leading to labelling of the N-terminal arginine peptide.

UI	MeSH Term	Description	Entries
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
D009132	Muscles	Contractile tissue that produces movement in animals.	Muscle Tissue,Muscle,Muscle Tissues,Tissue, Muscle,Tissues, Muscle
D003432	Cross-Linking Reagents	Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.	Bifunctional Reagent,Bifunctional Reagents,Cross Linking Reagent,Crosslinking Reagent,Cross Linking Reagents,Crosslinking Reagents,Linking Reagent, Cross,Linking Reagents, Cross,Reagent, Bifunctional,Reagent, Cross Linking,Reagent, Crosslinking,Reagents, Bifunctional,Reagents, Cross Linking,Reagents, Cross-Linking,Reagents, Crosslinking
D000263	Adenylate Kinase	An enzyme that catalyzes the phosphorylation of AMP to ADP in the presence of ATP or inorganic triphosphate. EC 2.7.4.3.	Myokinase,AMP Kinase,ATP-AMP Phosphotransferase,ATP-AMP Transphosphorylase,Adenylokinase,ATP AMP Phosphotransferase,ATP AMP Transphosphorylase,Kinase, AMP,Kinase, Adenylate,Phosphotransferase, ATP-AMP,Transphosphorylase, ATP-AMP
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D001386	Azides	Organic or inorganic compounds that contain the -N3 group.	Azide
D013379	Substrate Specificity	A characteristic feature of enzyme activity in relation to the kind of substrate on which the enzyme or catalytic molecule reacts.	Specificities, Substrate,Specificity, Substrate,Substrate Specificities
D013552	Swine	Any of various animals that constitute the family Suidae and comprise stout-bodied, short-legged omnivorous mammals with thick skin, usually covered with coarse bristles, a rather long mobile snout, and small tail. Included are the genera Babyrousa, Phacochoerus (wart hogs), and Sus, the latter containing the domestic pig (see SUS SCROFA).	Phacochoerus,Pigs,Suidae,Warthogs,Wart Hogs,Hog, Wart,Hogs, Wart,Wart Hog