Decarboxylative amination

Esterolysis, decarboxylation, amination, deamination and oxidoreduction are catabolic enzyme activities of proteinoids and proteinoid microspheres. The formation... 

Since several kinds of reaction have been shown to be catalyzed by thermal polyamino acids, the discovery of other kinds of reaction seems likely to occur on further examination. Those reactions already studied include hydrolysis, decarboxylation, amination, and one instance of deamination. Assemblage of some of the reactions catalyzed reflect metabolic sequences, as laid out in a flow sheet in the section on pathways (Section IV, E). Within these sequences, some specificity in reaction between proteinoid and substrate can be observed. As stated before, some activities of thermal polymers have been shown to be influenced by, or to be dependent on, cofactors. 

A complimentary approach was reported by Minakata, who used the same reagent combination within a sequential decarboxylation/amination strategy [77]. In this work, several allylic carboxylic acids 123 were submitted to decarboxylative amination to give the corresponding products 124 in very good yields. 

A novel intramolecular decarboxylative amination protocol of A -tosylcarbamates (10) for the synthesis of axially chiral allenes containing synthetically attractive functionalities (11) has been developed with excellent enantioselectivities (up to 92% ee) and good yields (Scheme 5). The biphenyl backbone in the ligands has been found responsible 0... 

Decarboxylation of amino acids can also proceed as a non-enzymatic reaction. Analogously to the enzyme catalysed decarboxylations, amines are formed as byproducts of the Strecker degradation of amino acids and by thermal decarboxylation of amino acids, especially of sulfur amino acids, hydroxyamino acids and aromatic amino acids. For example, thermal decarboxylation and subsequent reactions of cysteine and cystine produce ammonia... 

The mechanism of this enzymic reaction, catalyzed by pyridoxal phosphate, has been discussed above as pathway b (Section 4). The net result is the production of CO2 and a primary amine, whose formula can easily be derived from the amino acid which was decarboxylated. Amines of this type are called biogenic amines (Guggenheim) many of them possess a strong pharmacologic effect, and others are important as precursors of hormones and as components of coenzymes and other active substances. 

Girard, P, Guillot, N., Motherwell, W.B., and Potier, P, Observations on the reaction of O-acylthiohydroxamates with thionitrite esters a novel free radical chain reaction for decarboxylative amination, /. Chem. Soc., Chem. Commun., 2385,1995. 

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