Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives
Lactic acid (LA) is a natural organic acid that can be used in a wide variety of industries. Recently, the production of lactic acid by fermentation protocols has gained relevance. However, these biotechnological processes often encounter challenges in the production of enantiopure D- or L-lactic ac...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-06-01
|
| Series: | Applied Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3417/15/12/6433 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1839654959666167808 |
|---|---|
| author | Maria Montrone Cosimo Cardellicchio Maria Annunziata M. Capozzi |
| author_facet | Maria Montrone Cosimo Cardellicchio Maria Annunziata M. Capozzi |
| author_sort | Maria Montrone |
| collection | DOAJ |
| description | Lactic acid (LA) is a natural organic acid that can be used in a wide variety of industries. Recently, the production of lactic acid by fermentation protocols has gained relevance. However, these biotechnological processes often encounter challenges in the production of enantiopure D- or L-lactic acid. Thus, the measurement and control of the enantiopurity of lactic acid and its derivatives is a crucial step in these productions, especially when monomers have to be used to synthesize polymers, such as polylactic acid (PLA). In the present work, we propose a measurement of the enantiopurity of lactic acid mixtures with HPLC-DAD by using direct-phase conditions, which are mild, and a large set of different employable chiral columns. To this end, we report the synthesis of two new LA derivatives (2-nitrobenzyl 2-hydroxypropanoate and 2,4-dinitrobenzyl 2-hydroxypropanoate) and benzyl 2-hydroxypropanoate, with a selective and non-racemizing chemical functionalization. Then, three commercially available HPLC direct-phase chiral columns are tested to achieve a method for measuring the enantiomeric purity of lactic acid derivatives. The 2-nitrobenzyl lactate was chosen as the best lactic acid derivative and the Chiralpak IA column was chosen as the most effective chiral column to achieve a new and efficient protocol (Rs = 3.57 and α = 1.13) for the measurement of the enantiopurity of lactic acid. |
| format | Article |
| id | doaj-art-28e42f91b23a44499edd1e5fbda4dbca |
| institution | Matheson Library |
| issn | 2076-3417 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj-art-28e42f91b23a44499edd1e5fbda4dbca2025-06-25T13:24:36ZengMDPI AGApplied Sciences2076-34172025-06-011512643310.3390/app15126433Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid DerivativesMaria Montrone0Cosimo Cardellicchio1Maria Annunziata M. Capozzi2Dipartimento di Chimica, Università di Bari, Via Orabona 4, 70126 Bari, ItalyCNR ICCOM, Dipartimento di Chimica, Università di Bari, Via Orabona 4, 70126 Bari, ItalyDipartimento di Chimica, Università di Bari, Via Orabona 4, 70126 Bari, ItalyLactic acid (LA) is a natural organic acid that can be used in a wide variety of industries. Recently, the production of lactic acid by fermentation protocols has gained relevance. However, these biotechnological processes often encounter challenges in the production of enantiopure D- or L-lactic acid. Thus, the measurement and control of the enantiopurity of lactic acid and its derivatives is a crucial step in these productions, especially when monomers have to be used to synthesize polymers, such as polylactic acid (PLA). In the present work, we propose a measurement of the enantiopurity of lactic acid mixtures with HPLC-DAD by using direct-phase conditions, which are mild, and a large set of different employable chiral columns. To this end, we report the synthesis of two new LA derivatives (2-nitrobenzyl 2-hydroxypropanoate and 2,4-dinitrobenzyl 2-hydroxypropanoate) and benzyl 2-hydroxypropanoate, with a selective and non-racemizing chemical functionalization. Then, three commercially available HPLC direct-phase chiral columns are tested to achieve a method for measuring the enantiomeric purity of lactic acid derivatives. The 2-nitrobenzyl lactate was chosen as the best lactic acid derivative and the Chiralpak IA column was chosen as the most effective chiral column to achieve a new and efficient protocol (Rs = 3.57 and α = 1.13) for the measurement of the enantiopurity of lactic acid.https://www.mdpi.com/2076-3417/15/12/6433enantiomeric puritylactic acidHPLC-DADchiral direct phasePLA |
| spellingShingle | Maria Montrone Cosimo Cardellicchio Maria Annunziata M. Capozzi Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives Applied Sciences enantiomeric purity lactic acid HPLC-DAD chiral direct phase PLA |
| title | Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives |
| title_full | Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives |
| title_fullStr | Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives |
| title_full_unstemmed | Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives |
| title_short | Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives |
| title_sort | alternative hplc dad direct phase approach to measurement of enantiopurity of lactic acid derivatives |
| topic | enantiomeric purity lactic acid HPLC-DAD chiral direct phase PLA |
| url | https://www.mdpi.com/2076-3417/15/12/6433 |
| work_keys_str_mv | AT mariamontrone alternativehplcdaddirectphaseapproachtomeasurementofenantiopurityoflacticacidderivatives AT cosimocardellicchio alternativehplcdaddirectphaseapproachtomeasurementofenantiopurityoflacticacidderivatives AT mariaannunziatamcapozzi alternativehplcdaddirectphaseapproachtomeasurementofenantiopurityoflacticacidderivatives |