Leung Anna E, Raba Andreas, Beckerle Klaus, Allgaier Jürgen, Wacklin-Knecht Hanna P
European Spallation Source ERIC, P.O. Box 176, 221 00 Lund, Sweden.
Jülich Centre for Neutron Science (JCNS-1), Forschungszentrum Jülich GmbH, Leo Brandt Straße, 52425 Jülich, Germany.
Bioengineering (Basel). 2025 May 27;12(6):575. doi: 10.3390/bioengineering12060575.
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- monomers were synthesized from sodium pyruvate- using D- and L-lactate dehydrogenase enzymes (D-LDH and L-LDH) as biocatalysts. The reduced form of the co-enzyme nicotinamide adenine dinucleotide- (NADH-) was generated in situ from the oxidized form nicotinamide adenine dinucleotide (NAD) by formate dehydrogenase (FDH)-catalyzed oxidation of sodium formate- to carbon dioxide with concerted reduction of NAD to NADH-. 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.
我们报道了通过氘代丙交酯的聚合反应合成具有明确分子量的高对映体纯的全氘代聚-L-乳酸和聚-D-乳酸聚合物。使用D-乳酸脱氢酶（D-LDH）和L-乳酸脱氢酶（L-LDH）作为生物催化剂，由丙酮酸钠合成了对映体纯的D-和L-乳酸单体。辅酶烟酰胺腺嘌呤二核苷酸（NADH）的还原形式是通过甲酸脱氢酶（FDH）催化甲酸钠氧化为二氧化碳并将NAD协同还原为NADH，由烟酰胺腺嘌呤二核苷酸（NAD）的氧化形式原位生成的。为了将全氘代乳酸单体转化为相应的丙交酯二聚体，我们开发了一种方法，以生成最终阴离子开环聚合步骤所需的高纯度这些化合物。该方法能够生成一系列全氘代聚乳酸聚合物，这些聚合物非常适合使用对氘敏感的中子散射、红外和核磁共振光谱方法来表征聚合物结构和动力学。此外，这些氘标记的聚合物非常适合用于研究基于聚乳酸的塑料的生物降解。
