56066-92-3Relevant academic research and scientific papers
Rationalisation of the regioselective hydrolysis of aliphatic dinitriles with Rhodococcus rhodochrous AJ270
Meth-Cohn, Otto,Wang, Mei-Xiang
, p. 1041 - 1042 (2007/10/03)
Aliphatic dinitriles undergo regioselective hydrolysis with the title organism to give monoacids with up to four methylenes between the nitrile functions (optimally 2-3) or when either an oxygen is placed β, γ or δ to the nitrile (δ-placement being optimal) or β or γ (optimally γ) but not δ sulfur substituents are present; nitrogen substituents appear to behave as for oxygen but suffer a steric limitation of the size of the nitrogen substituent.
Regioselective biotransformations of dinitriles using Rhodococcus sp. AJ270
Meth-Cohn, Otto,Wang, Mei-Xiang
, p. 3197 - 3204 (2007/10/03)
A variety of dinitriles have been hydrolysed selectively under very mild conditions using Rhodococcus sp. AJ270. Aliphatic dinitriles NC[CH2]nCN 1 undergo regioselective hydrolysis to give the mono acids 2 with up to 4 methylenes between the nitrile functions while those with n > 4 give the diacids 3 in good yield. Dinitriles NC[CH2]nX[CH2]nCN 4 bearing an ether or sulfide linkage are efficiently transformed into the mono acids 5 when an oxygen is placed β, γ or δ to the cyano group or a β- or γ-sulfur is present. Hydrolysis of N,N-bis(2-cyanoethyl)anilines 4h-j takes place slowly affording exclusively the monoacids 5h-j while the monocyano amides 5o-p are obtained as the sole isolable product from rapid hydrolysis of the corresponding N,N-bis(2-cyanomethyl)butylamine 4o and N,N-bis(3-cyanopropyl)butylamine 4p. Higher homologues of arylimino- and butylimino-dinitriles are inert to enzymatic hydrolysis. A variety of other aliphatic dinitriles have been converted readily into mono acids in good to excellent yields except for o-phenylenediacetonitrile which gives o-phenylenediacetamide as the major product. The title organism also effects the hydrolysis of aromatic dinitriles with regiocontrol such as m- and p-dicyanobenzenes, but nct the ortho-substituted analogue. The scope and limitations of this enzymatic process have been systematically studied and the mechanism of regioselective hydrolysis has been discussed in terms of a chelation-deactivation effect.
