1,5-Diaminopentane

1,5-Diaminopentane, also known as cadaverine, is an important industrial platform chemical (figure 1). It is a colorless, smoky liquid with an ammonia-like odor, which is easily soluble in water and ethanol. Similar to putrescine (1,4-diaminobutane), 1,5-diaminopentane serves as a component of polymers such as polyamides and polyurethane, chelating agents, and other additives. In the rising era of bioeconomy, the five-carbon compound 1,5-diaminopentane receives increasing interest.

Fig. 1 Structure of 1,5-diaminopentane

Metabolism of 1,5-Diaminopentane

The most promising development for bio-based supply of 1,5-diaminopentane is microbial production using genetically engineered microorganism like Corynebacterium glutamicum or Escherichia coli.

Systems metabolic engineering of E. coliSystems metabolic engineering of C. glutamicum

In E. coli, diaminopentane is synthesized via the lysine pathway. Branching off the tricarboxylic acid (TCA) cycle, the biosynthetic pathway starts from oxaloacetate. Requiring additional one molecule of pyruvate, two ammonium molecules, and four nicotinamide adenine dinucleotide phosphate (NADPH) molecules, it then proceeds via ten successive steps^[1].

Fig. 2 The pathways involved in diaminopentane metabolism in E. coli combined with the strategies for metabolic engineering for diaminopentane overproduction.

In a pioneering study, a C. glutamicum wild type was modified by replacing homoserine dehydrogenase with heterologous lysine decarboxylase (cadA) from E. coli. The obtained strain TM45 secreted diaminopentane in small amounts, providing a valuable proof of concept to produce this novel metabolite in C. glutamicum. Production could be increased via stronger expression of cadA using a plasmid with a strong constitutive promoter and kanamycin as selection pressure^[1].

Fig. 3 The pathways involved in diaminopentane metabolism in C. glutamicum combined with the strategies for metabolic engineering for diaminopentane overproduction.

Applications

As mentioned before, 1,5-diaminopentane is an attractive building block for polymers such as polyamides and polyurethane, chelating agents, and other additives. Particularly, it is relevant for bio-polyamides derived from renewable feedstocks to replace conventional polyamides from petrochemical routes which suffer from shortage and rising prices of the fossil resources as well as low eco-efficiency.

For instance, bio-based 1,5-diaminopentane combines with appropriate bio-blocks such as succinate or sebacic acid from castor oil to provide completely bio-based polyamides such as PA 5.4 and PA 5.10, respectively (figure 4).

Fig. 4 Polymerization of diaminopentane with succinic acid or sebacic acid to build PA 5.4 or PA 5.10

Our 1,5-Diaminopentane

Our 1,5-diaminopentane is made from renewable plant resource. The bio-based carbon content of our 1,5-diaminopentane is 100% which is tested according to ASTM 6866. This effectively reduces the use of petrochemicals, and thus carbon emissions are reduced. The basic properties of our biosynthetic 1,5-diaminopentane are showed as followings:

Alfa Chemistry is a professional supplier of biosynthetic 1,5-diaminopentane. For high quality products, professional technical service, use suggestion and latest industry news, please feel free to contact us.

Reference

1. Kind S, Wittmann C. Bio-based production of the platform chemical 1,5-diaminopentane. Appl Microbiol Biotechnol. 2011 Sep;91(5):1287-96.

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