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Synthesis of Cyclic Polyamines by Enzymatic Generation of an Amino Aldehyde In Situ
Author(s) -
Cassimjee Karim Engelmark,
Marín Sílvia Rodríguez,
Berglund Per
Publication year - 2012
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201200347
Subject(s) - polyamine , amino acid , chemistry , aldehyde , alcohol dehydrogenase , alcohol , yield (engineering) , enzyme , organic chemistry , aldehyde dehydrogenase , stereochemistry , biochemistry , catalysis , materials science , metallurgy
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.