A method for identifying the absolute configuration and optical purity of amino acids and peptide compounds
A technology of absolute configuration and optical purity, applied in the field of chiral recognition of amino acids, can solve the problems of poor sensitivity, large amount of reagents, long time consumption, etc., and achieve the effect of high sensitivity, small amount of sample, simple and rapid determination
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Embodiment 1
[0065] Taking 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 make 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 respectively. Then, mix 100 μL L-phenylalanine solution and 100 μL o-phthalaldehyde solution, shake for 1 min, and 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 phthalaldehyde was added to L-phenylalanine and shaken for 1 min, the ECD spectrum of the reaction solution (1c) showed a...
Embodiment 2
[0075] Structure Determination of Derivatized Products of L-Alanine
[0076]
[0077] Taking L-alanine and L-phenylalanine as examples to illustrate the chemical structures of the derivatized products 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 an eggplant-shaped bottle, stir to mix evenly, then add 67 mg of o-phthalaldehyde, stir at room temperature for 1 min, and prepare a pure derivatized product by medium pressure. L-alanine derivatized products 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, foun...
Embodiment 3
[0080] Structure Determination of Derivatized Products of L-Phenylalanine
[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 an eggplant-shaped bottle, stir to mix evenly, then add 67 mg of o-phthalaldehyde, stir at room temperature for 1 min, and prepare a pure derivatized product by medium pressure. L-Phenylalanine Derivatized Products 1 H-NMR, 13 The C-NMR and HRMS spectra are listed in Figure 7-Figure 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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