2-Amino-1,3-propanediol

Description

2-Amino-1,3-propanediol (2-APD, also known as serinol) is a high-value-added chemical that is used as a building block for the synthesis of a variety of compounds, including drugs to treat type 2 diabetes mellitus, the antibiotic chloramphenicol, immune multiple sclerosis, and a new generation of nonionic X-ray contrast agents.

Chemical properties

white to off-white adhering crystalline powder. 2-Amino-1,3-propanediol (1,3-dihydroxy-isopropylamine, aminoglycerin or amino-trimethylenglykol) has a molecular formula of C3H9NO2, belongs to the group of amino alcohols and is prochiral. As it is a structural analogue to the amino acid serine, the common designation is serinol. It is very stable, corrosive, hygroscopic, and dissolves very well in water. It has a molecular weight of 91.11 g/mol, melts at 52 to 56 °C, and has a boiling point of 115 to 116 °C.

The Uses of 2-Amino-1,3-propanediol

2-Amino-1,3-propanediol is used as an intermediate in several chemical applications and is also useful for serinol and some of its derivatives. Serinol may be used to prepare the artificial nucleic acids. It may be used in the synthesis of N-acylated serinol and C16-serinol affinity gel.

Preparation

Add 20% 2-nitro-1,3-propanediol methanol solution (1250 g) to 5% palladium/carbon 3.5 g. Hydrogen (70 L, pressure 3MPa) was continuously introduced and reacted at 75°C for 5 hours to obtain serine alcohol solution. The serine alcohol solution is pumped into a high vacuum distillation vessel, vacuumed to 40 pa, and methanol is distilled for reuse. Yield = 97.2%.

Biosynthesis

Currently, the manufacture of 2-Amino-1,3-propanediol (2-APD) predominantly relies on chemical processes by utilizing fossil fuel-derived and highly explosive raw materials. In addition to chemical synthesis, its synthesis can also rely on biosynthesis. Luo et al. established an artificial biosynthetic pathway for converting glucose to 2-APD in a metabolically engineered Escherichia coli. This artificial pathway employs an engineered heterogeneous aminotransferase RtxA for diverting dihydroxyacetone phosphate (DHAP) to generate 2-APD phosphate and an endogenous phosphatase for converting it into the target product 2-APD. 2-APD-P is 2-amino-1,3-propanediol phosphate[1].

Origin

In the 1970s, 2-Amino-1,3-propanediol (2-APD) was first reported to be a molecular building block of the natural products rhizobitoxine and dihydrorhizobitoxine produced by the legume symbiont Rhizobium japonicum[1].

General Description

Serinol activates toxin production in the attenuated cultures of Helminthosporium sacchari. Preparation of polyesters derived from serinol is reported.

Source

Serinol is a non-toxic, odourless, biodegradable chemical substance obtained from both natural and petrochemical feedstocks. In fact, serinol has been synthesized from oil-based precursors such as 2-nitro-1,3-propanediol, nitromethane, dihydroxyacetone (DHA), dihydroxyacetone oxime, and 5-amino-1,3-dioxane, but it can also be prepared from the biomolecule glycerol. It was found to occur in renewable sources, such as sugar cane (Saccharum officinarum) or as a metabolite from sponge (Stelletta Inconspicua). Moreover, since serinol is structurally analogous to serin, its preparation starting from this amino acid has been reported.

References

[1] Luo Y, et al. An Artificial Biosynthetic Pathway for 2?Amino-1,3-Propanediol Production Using Metabolically Engineered Escherichia coli. ACS Synthetic Biology, 2019; 8: 548–556.