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Synthesis of cyclic polyamines by enzymatic generation of an amino aldehyde in situ
KTH, School of Biotechnology (BIO), Biochemistry.
KTH, School of Biotechnology (BIO), Biochemistry.
KTH, School of Biotechnology (BIO), Biochemistry.ORCID iD: 0000-0002-9577-832X
2012 (English)In: Macromolecular rapid communications, ISSN 1022-1336, E-ISSN 1521-3927, Vol. 33, no 18, 1580-1583 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2012. Vol. 33, no 18, 1580-1583 p.
Keyword [en]
enzyme catalysis, hydrophilic polymers, polyamines, polyelectrolytes, self-assembly
National Category
Biochemistry and Molecular Biology
URN: urn:nbn:se:kth:diva-103545DOI: 10.1002/marc.201200347ISI: 000308716200014ScopusID: 2-s2.0-84866433787OAI: diva2:560486

QC 20121015

Available from: 2012-10-15 Created: 2012-10-15 Last updated: 2012-10-25Bibliographically approved

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