Biomaterial Database

Mechanistic considerations of guanidine-catalyzed reactions. 2011

Xiao Fu, and Choon-Hong Tan

Department of Chemistry, 3 Science Drive 3, National University of Singapore, Singapore 117543.

This feature article discusses the various mechanistic aspects of guanidine-catalyzed reactions. Guanidines are well known as strong organic bases; however, in the first section, three most common commercially available guanidines, TMG, TBD and MTBD, will be used to illustrate the use of guanidines as nucleophilic catalysts. In the second section, different modes of hydrogen bonding interactions of the conjugate acid of guanidine, the guanidinium, are discussed. Particularly interesting are the possibilities of mono-functional or bifunctional activation of a nucleophile and an electrophile by guanidinium.

UI	MeSH Term	Description	Entries
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D006146	Guanidines	A family of iminourea derivatives. The parent compound has been isolated from mushrooms, corn germ, rice hulls, mussels, earthworms, and turnip juice. Derivatives may have antiviral and antifungal properties.
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
D018360	Crystallography, X-Ray	The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies
D019791	Guanidine	A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.	Guanidine Hydrochloride,Guanidinium,Guanidinium Chloride,Guanidine Monohydrate,Guanidine Monohydrobromide,Guanidine Monohydrochloride,Guanidine Monohydroiodine,Guanidine Nitrate,Guanidine Phosphate,Guanidine Sulfate,Guanidine Sulfate (1:1),Guanidine Sulfate (2:1),Guanidine Sulfite (1:1),Guanidium Chloride,Chloride, Guanidinium,Chloride, Guanidium,Hydrochloride, Guanidine,Monohydrate, Guanidine,Monohydrobromide, Guanidine,Monohydrochloride, Guanidine,Monohydroiodine, Guanidine,Nitrate, Guanidine,Phosphate, Guanidine,Sulfate, Guanidine