Tris(2-carbonylethyl)phosphoric acid hydrochloride (TCEP-HCI) is
a novel reducing agent and deprotecting agent for thiolated DNA.
Tris(2-carbonylethyl)phosphoric acid hydrochloride (TCEP HCI) is more
stable and more compatible than the conventional reducing agent and
deprotecting agent mercaptoethanol or dithiothreitol (DTT). TCEP-HCI is recognized as an ideal reducing agent without any irritating odor .
At
present, there are mainly the following methods for the synthesis route
of tris(2-carbonylethyl)phosphoric acid hydrochloride (TCEP -HCI):
The
first method: Reacting phosphine with phosphine PH 3 as a raw material
in an autoclave, followed by hydrolysis to obtain
tris(2-carbonylethyl)phosphoric acid hydrochloride (TCEP-HCI). Although
this method has a high yield, the autoclave and the highly toxic gas
phosphine need to be used in the reaction process, and the risk factor
is high, which is not conducive to industrial production.
The
second method: Using tetramethylolphosphonium chloride as a raw
material to react with acrylonitrile. Finally, it was hydrolyzed with
concentrated hydrochloric acid to give the product. The steps of this
method are simple, but it uses tetramethylolphosphonium chloride to
replace the highly toxic gas phosphine to synthesize
tricyanoethylphosphine, but tris-cyanoethyl phosphate is hydrolyzed to
give tris(2-carbonylethyl)phosphoric acid hydrochloride (TCEP). A solid
mixture of hydrochloride and ammonium chloride, the two salts of the
mixture can not achieve effective separation, the product purity is low.
The third
method: talkylation reaction of tetramethylolphosphorus chloride and
the compound in an organic solvent in the presence of a base yields
trimethyl 3, 3 ', 3' '-phosphine triyl tripropionate, Then hydrolysis
reaction occurs in concentrated hydrochloric acid to obtain the
compound TCEP-HCl. This method is easy to operate, has low cost and high
yield, and is suitable for industrial production.
Related links:High Purity TCEP-HCI
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