Solid-supported cyanoborohydride cartridges for automation of reductive amination radiochemistry

Reductive methylation of proteins with sodium cyanoborohydride

Reductive methylation of protein amino groups with formaldehyde and sodium cyanoborohydride is shown to give up to 25% yield of N-cyanomethyl (-CH2CN) product; on work up of the reaction this is hydrolysed back to starting amine, lowering the methylation yield. Addition of metal ions such as Ni2+, which complex with free cyanide ion, improve reductive methylation yields by suppressing by-produc...

Transamination and Reductive Amination

Æ-Keto acids can be reductively aminated to Æ-amino acids via amino acid dehydrogenase catalysis, with NAD(P)H as cofactor. The nitrogen source for the amine functionality is ammonia, the least expensive source. Regeneration of the co-factor NAD(P)+ back to NAD(P)H is required for synthesis and is commonly afforded via formate dehydrogenase catalyzed oxidation of formate to carbon dioxide or gl...

DNA-catalyzed reductive amination.

Deoxyribozymes are particular DNA sequences that have catalytic ability, analogous to protein enzymes as functional amino acid sequences. The discovery of natural RNA enzymes (ribozymes) spurred the search for artificial deoxyribozymes, which are identified by in vitro selection. Most deoxyribozyme-catalyzed reactions involve phosphodiester bond cleavage or ligation, although other reactions su...

Enantioselective organocatalytic reductive amination.

The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines and provided a highly stereoselective method for the reductive amination of heterocyclic amines. A diverse spectrum of ketone and amine substrat...

Formal asymmetric biocatalytic reductive amination.