Marking method and selective adsorption method for phosphorylating peptide, coordination compound used for the same method and producing method for the same coordination compound
A technology of coordination compounds and phosphorylated peptides, which can be applied in the preparation methods of peptides, compounds of elements of Group 5/15 of the periodic table, zinc organic compounds, etc., and can solve the problems of low coordination and binding function of phosphodiester groups.
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[0087] The preparation method of compound (VIII) is not limited to the method shown in Reaction Scheme 2, for example, compound (VIII) can be synthesized from compound (VI) and halide.
[0088] Next, compound (II) can be produced from the reaction of compound (IX). This reaction can adopt conventional tertiary amine synthesis reaction. For example, it is condensed in the presence of a base in a solvent. In this step, according to R 1 Depending on the difference, an appropriate protecting group can also be introduced and deprotected. Alternatively, substituting R in compound (IX) 1 , using compounds with inactive substituent groups. After performing the above steps, the above-mentioned inert substituent is changed to R by changing the functional group 1 , and thus, compound (II) can also be synthesized. For example, a compound containing a nitro group is used as the above-mentioned inert substituent, and the nitro group is converted to an amino group which is a reactive g...
manufacture example 1-1
[0096] Production Example 1-1 Methyl 6-bromomethylnicotinate
[0097]
[0098] To a solution of 50 g (331 mmol) of methyl 6-methylnicotinate in carbon tetrachloride (625 mL), 59 g (331 mmol) of N-bromosuccinimide and 1.0 g of benzoyl peroxide were added. Then, it was reacted at 40-50° C. for 24 hours while performing light irradiation with a light emitter.
[0099] After the reaction solution was cooled, the precipitated crystals were filtered, and the filtrate was washed with an aqueous sodium bicarbonate solution and then concentrated. The resulting residue was purified by silica gel column chromatography to obtain 37 g of the intended product. The NMR test results are as follows:
[0100] 1 H-NMR (CDCl 3 , 300MHz): δ3.96 (3H, s, OCH 3 ), 4.58 (2H, s, CH 2 Br), 7.54 (1H, d, Py), 8.30 (1H, dd, Py), 9.17 (1H, d, Py).
manufacture example 1-2
[0101] Production Example 1-2 N,N,N'-tris(2-pyridylmethyl)-1,3-diaminopropan-2-ol
[0102]
[0103] To a solution of 32.6 g (362 mmol) of 1,3-diaminopropan-2-ol in methanol (2400 mL), 60 mL of concentrated hydrochloric acid was added, and 116.3 g (1.09 mol) of 2-pyridinealdehyde was added dropwise. Then, 50.16 g (798 mmol) of sodium cyanotrihydroborate was added. After the addition was complete, the reaction was carried out at room temperature for 3 days.
[0104] Concentrated sulfuric acid was added to the reaction solution to adjust the pH to 6, then concentrated to a certain extent, 0.1N aqueous sodium hydroxide solution was added to adjust the pH to 7, and extracted with chloroform. The chloroform layer was collected, dried and concentrated. The resulting residue was purified by silica gel column chromatography to obtain 34 g of the intended product. The NMR test results are as follows:
[0105] 1 H-NMR (CDCl 3 , 300MHz): δ2.59-2.83 (4H, m, CH 2 ), 3.86-4.01 (7H,...
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