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The Enzymatic Synthesis of Perdeuterated D- and L-Lactic Acid-d4 and Polymerization of Their Lactides to Polylactic Acid

Leung, Anna E. ; Raba, Andreas ; Beckerle, Klaus ; Allgaier, Jürgen and Wacklin-Knecht, Hanna P. LU orcid (2025) In Bioengineering 12(6).
Abstract

We report the synthesis of highly enantiopure perdeuterated
poly-L-lactic acid and poly-D-lactic acid polymers with well-defined
molecular weight by polymerization of perdeuterated lactides.
Enantiopure D- and L-lactic acid-d4 monomers were synthesized from sodium pyruvate-d3
using D- and L-lactate dehydrogenase enzymes (D-LDH and L-LDH) as
biocatalysts. The reduced form of the co-enzyme nicotinamide adenine
dinucleotide-d1 (NADH-d1) was generated in situ from the oxidized form nicotinamide adenine dinucleotide (NAD+) by formate dehydrogenase (FDH)-catalyzed oxidation of sodium formate-d1 to carbon dioxide with concerted reduction of... (More)

We report the synthesis of highly enantiopure perdeuterated
poly-L-lactic acid and poly-D-lactic acid polymers with well-defined
molecular weight by polymerization of perdeuterated lactides.
Enantiopure D- and L-lactic acid-d4 monomers were synthesized from sodium pyruvate-d3
using D- and L-lactate dehydrogenase enzymes (D-LDH and L-LDH) as
biocatalysts. The reduced form of the co-enzyme nicotinamide adenine
dinucleotide-d1 (NADH-d1) was generated in situ from the oxidized form nicotinamide adenine dinucleotide (NAD+) by formate dehydrogenase (FDH)-catalyzed oxidation of sodium formate-d1 to carbon dioxide with concerted reduction of NAD+ to NADH-d1.
For the conversion of the perdeuterated lactic acid monomers to the
corresponding lactide dimers, we developed a process for generating
these compounds in the high purity needed for the final anionic
ring-opening polymerization step. This method enabled the generation of a
range of perdeuterated polylactic acid polymers that are highly
suitable for the characterization of polymer structure and dynamics
using neutron scattering, infrared and nuclear magnetic resonance
spectroscopy methods that are sensitive to deuterium. Furthermore, these
deuterium-labeled polymers are well-suited to the study of the
biodegradation of PLA-based plastics.

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Please use this url to cite or link to this publication:
author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
biopolymers, deuteration, enzymatic, polylactic acid, synthesis
in
Bioengineering
volume
12
issue
6
article number
575
pages
14 pages
publisher
MDPI AG
external identifiers
  • pmid:40564392
  • scopus:105009135743
ISSN
2306-5354
DOI
10.3390/bioengineering12060575
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2025 by the authors.
id
c6d3b140-4547-41f0-b912-3c4cf5bef2ad
date added to LUP
2025-12-17 13:27:36
date last changed
2025-12-19 10:11:46
@article{c6d3b140-4547-41f0-b912-3c4cf5bef2ad,
  abstract     = {{<p>We report the synthesis of highly enantiopure perdeuterated <br>
poly-L-lactic acid and poly-D-lactic acid polymers with well-defined <br>
molecular weight by polymerization of perdeuterated lactides. <br>
Enantiopure D- and L-lactic acid-d<sub>4</sub> monomers were synthesized from sodium pyruvate-d<sub>3</sub><br>
 using D- and L-lactate dehydrogenase enzymes (D-LDH and L-LDH) as <br>
biocatalysts. The reduced form of the co-enzyme nicotinamide adenine <br>
dinucleotide-d<sub>1</sub> (NADH-d<sub>1</sub>) was generated in situ from the oxidized form nicotinamide adenine dinucleotide (NAD<sup>+</sup>) by formate dehydrogenase (FDH)-catalyzed oxidation of sodium formate-d<sub>1</sub> to carbon dioxide with concerted reduction of NAD<sup>+</sup> to NADH-d<sub>1</sub>.<br>
 For the conversion of the perdeuterated lactic acid monomers to the <br>
corresponding lactide dimers, we developed a process for generating <br>
these compounds in the high purity needed for the final anionic <br>
ring-opening polymerization step. This method enabled the generation of a<br>
 range of perdeuterated polylactic acid polymers that are highly <br>
suitable for the characterization of polymer structure and dynamics <br>
using neutron scattering, infrared and nuclear magnetic resonance <br>
spectroscopy methods that are sensitive to deuterium. Furthermore, these<br>
 deuterium-labeled polymers are well-suited to the study of the <br>
biodegradation of PLA-based plastics.</p>}},
  author       = {{Leung, Anna E. and Raba, Andreas and Beckerle, Klaus and Allgaier, Jürgen and Wacklin-Knecht, Hanna P.}},
  issn         = {{2306-5354}},
  keywords     = {{biopolymers; deuteration; enzymatic; polylactic acid; synthesis}},
  language     = {{eng}},
  number       = {{6}},
  publisher    = {{MDPI AG}},
  series       = {{Bioengineering}},
  title        = {{The Enzymatic Synthesis of Perdeuterated D- and L-Lactic Acid-<i>d</i><sub>4</sub> and Polymerization of Their Lactides to Polylactic Acid}},
  url          = {{http://dx.doi.org/10.3390/bioengineering12060575}},
  doi          = {{10.3390/bioengineering12060575}},
  volume       = {{12}},
  year         = {{2025}},
}