Method for identifying absolute configuration and optical purity of amino acid and peptide compounds
A technology with absolute configuration and optical purity, applied in the field of chiral recognition of amino acids, can solve the problems of time-consuming, poor sensitivity, and large amount of reagents, and achieve the effect of less sample amount, high sensitivity, simple and fast determination
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Embodiment 1
[0065] Take L-phenylalanine as an example to introduce its chiral recognition process
[0066] (1) Derivatization reaction
[0067] Dissolve 16.5 mg of L-phenylalanine in 5 mL of KOH methanol solution to prepare a 0.02 mM solution, and dissolve 13.4 mg of o-phthalaldehyde in 10 mL of methanol. First, the ECD spectra of L-phenylalanine and o-phthalaldehyde were measured separately. Then, take 100 μL of L-phenylalanine solution and 100 μL of o-phthalaldehyde solution and mix, shake for 1 minute, and then perform ECD test.
[0068] (2) ECD detection of raw materials and derivatized products
[0069] ECD test results such as figure 1 Shown. There is no obvious Cotton effect in the ECD spectrum of the chiral recognition probe o-phthalaldehyde (1a). At the tested concentration, the ECD spectrum of L-phenylalanine (1b) has a positive Cotton effect at 210nm. When 0.5 equivalent of o-phthalaldehyde was added to L-phenylalanine and shaken for 1 min, the ECD spectrum of the reaction solution...
Embodiment 2
[0075] The structure determination of L-alanine derivatization product
[0076]
[0077] Taking L-alanine and L-phenylalanine as examples to illustrate the chemical structures of the derivatized products, they are Examples 2 and 3, respectively.
[0078] Take 56 mg of KOH solid and dissolve it in 5 mL of methanol solution. Add 89 mg of L-alanine and 5 mL of KOH methanol solution into the eggplant-shaped flask, stir to make it evenly mixed, then add 67 mg of o-phthalaldehyde, stir for 1 min at room temperature, and prepare the pure derivatized product by medium pressure. L-alanine derivatization product 1 H-NMR, 13 The C-NMR and HRMS spectra are listed in Figure 4-Figure 6 . 1 H-NMR(500MHz,DMSO-d 6 ): δ8.09(d,1H), 7.71(brs,2H), 7.55(d,1H), 4.87(d,1H), 4.72(d,1H), 4.59(brs,1H), 4.46(brs, 1H), 1.52 (dd, 6H). 13 C NMR(125MHz, DMSO-d 6 ):δ173.2,171.5,159.8,143.8,132.7,129.1,128.8,126.5,123.7,57.2,55.2,53.4,19.8,16.31.HRMS-ESI(calcd.for C 14 H 17 O 4 N 2 [M+H] + ) 277.1183, found 277.1...
Embodiment 3
[0080] The structure determination of L-phenylalanine derivatization product
[0081]
[0082] Take 56 mg of KOH solid and dissolve it in 5 mL of methanol solution. Add 165 mg of L-phenylalanine and 5 mL of KOH methanol solution into the eggplant-shaped flask, stir to mix them evenly, then add 67 mg of o-phthalaldehyde, stir for 1 min at room temperature, and prepare the pure derivatized product by medium pressure. L-phenylalanine derivatization product 1 H-NMR, 13 The C-NMR and HRMS spectra are listed in Figure 7-9 . 1 H-NMR(500MHz,DMSO-d 6 ): δ7.97 (d, 1H), 7.10-7.75 (m, 13H), 4.84 (brs, 1H), 4.54 (brs, 2H), 4.37 (dd, 1H), 3.25 (brs, 4H). 13 C NMR(125MHz, DMSO-d 6 ):δ172.6,171.0,161.9,143.5,140.5,139.3,132.8,130.0,129.1,128.8,126.8,126.7,123.7,63.6,62.1,53.3,38.6,36.1.HRMS-ESI(calcd.for C 26 H 25 O 4 N 2 [M+H]+)429.1809, found 429.1808.
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