title: Synthesis of cyclic polyamines by enzymatic generation of an amino aldehyde in situ.
abstract: Multifunctional polycationic polyamines, for example, used in drug and gene delivery, have product range limitations in their synthesis methods. Here, we synthesize a polyamine by forming a self-assembling amino aldehyde from the corresponding amino alcohol with horse liver alcohol dehydrogenase (HLADH), followed by reduction. Circular polyamines were synthesized from 3-amino-propan-1-ol as starting material, analogous to cyclic polyamines formed from azetidin. The product had an isolated yield of 89.7% or 15.3 g L(-1) . The predicted range of possible polyamine products by this method is broad since many amino alcohols are putative substrates for HLADH. The enzyme also had activity for 2-amino-propan-1-ol and 2-amino-2-phenyl-ethanol, for which the enantioselectivity was 330 (S) and 32 (R), respectively.
authors: School of Biotechnology, AlbaNova University Center, Stockholm, Sweden.
authors: Karim Engelmark
authors: KE
authors: Cassimjee
authors: Sílvia Rodríguez
authors: SR
authors: Marín
authors: Per
authors: P
authors: Berglund
mesh_terms: D000426:Alcohol Dehydrogenase / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D006736:Horses; D007700:Kinetics; D008099:Liver / Q000201:enzymology; D015394:Molecular Structure; D011073:Polyamines / Q000138:chemical synthesis* / Q000737:chemistry; D058105:Polymerization
chemical_list: D000447:Aldehydes; D011073:Polyamines; D000426:Alcohol Dehydrogenase