The Synthesis of Some Substituted Pyridine and Piperidine Compounds from Dipicolinic Acid†

Buchdahl, Myron R.; Soine, Taito O.

doi:10.1002/jps.3030410502

Cited by 2 publications

(1 citation statement)

References 5 publications

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“…DPA also prevents calcium salt precipitation in silver halide photographic solutions [5]. In chemical industry, it serves as precursor for the synthesis of pyridines and piperidines [6] and as a stabilizer of peroxides in aqueous solutions, e.g., in peroxycarboxylic acids and gels of organic peroxides by reducing the decomposition rate [7][8][9]. Furthermore, its antioxidative effect makes DPA interesting for use in pharmacy [10,11].…”

Section: Introductionmentioning

confidence: 99%

Metabolic Engineering of Corynebacterium glutamicum for Sustainable Production of the Aromatic Dicarboxylic Acid Dipicolinic Acid

et al. 2022

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Dipicolinic acid (DPA) is an aromatic dicarboxylic acid that mediates heat-stability and is easily biodegradable and non-toxic. Currently, the production of DPA is fossil-based, but bioproduction of DPA may help to replace fossil-based plastics as it can be used for the production of polyesters or polyamides. Moreover, it serves as a stabilizer for peroxides or organic materials. The antioxidative, antimicrobial and antifungal effects of DPA make it interesting for pharmaceutical applications. In nature, DPA is essential for sporulation of Bacillus and Clostridium species, and its biosynthesis shares the first three reactions with the L-lysine pathway. Corynebacterium glutamicum is a major host for the fermentative production of amino acids, including the million-ton per year production of L-lysine. This study revealed that DPA reduced the growth rate of C. glutamicum to half-maximal at about 1.6 g·L−1. The first de novo production of DPA by C. glutamicum was established by overexpression of dipicolinate synthase genes from Paenibacillus sonchi genomovar riograndensis SBR5 in a C. glutamicum L-lysine producer strain. Upon systems metabolic engineering, DPA production to 2.5 g·L−1 in shake-flask and 1.5 g·L−1 in fed-batch bioreactor cultivations was shown. Moreover, DPA production from the alternative carbon substrates arabinose, xylose, glycerol, and starch was established. Finally, expression of the codon-harmonized phosphite dehydrogenase gene from P. stutzeri enabled phosphite-dependent non-sterile DPA production.

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