The following compounds were prepared by this method:
L-Methionine Sulfoxide (5). Yield 97%. IR spectrum (KBr, ν, cm ): 1030 (S=O), 1520 (N–H), 1595 (C=O).
PMR spectrum (400 MHz, D O, δ, ppm): 2.40-2.43 (m, 2H, CH CH), 2.74 and 2.75 (2s, 3H, CH ), 3.00-3.15 (m, 2H, SCH ),
−
1
2
2
3
2
4
.14-4.18 (m, 1H, CH), 4.67-4.78 (m, 3H, NH , OH).
2
−
1
S-Methyl-L-cysteine Sulfoxide (6). Yield 97%. IRspectrum (KBr, ν, cm ): 1650 (C=O), 1510 (N–H), 1035 (S=O).
PMR spectrum (400 MHz, D O, δ, ppm): 2.83 and 2.84 (2s, 3H, CH ), 3.19-3.57 (m, 2H, CH ), 4.41-4.46 (m, 1H, CH), 4.71-
2
3
2
4
.91 (m, 3H, NH , OH).
2
−
1
S-Benzyl-L-cysteine Sulfoxide (7). Yield 95%. IR spectrum (KBr, ν, cm ): 1648 (C=O), 1500 (N–H), 1046 (S=O).
PMR spectrum (400 MHz, D O, δ, ppm): 2.18-2.34 (m, 2H, CH CH), 3.06 (m, 1H, CH), 3.66 and 3.69 (2s, 2H, CH C H ),
2
2
2 6 5
4
.99-5.10 (m, 3H, NH , OH), 6.55-6.69 (m, 5H, C H ).
2 6 5
−
1
Dialaninedisulfoxide (8). Yield 95%. IR spectrum (KBr, ν, cm ): 1648 (C=O), 1496 (N–H), 1048 (S=O). PMR
spectrum (400 MHz, D O, δ, ppm): 2.82-2.95 (m, 4H, 2 CH ), 3.87-3.89 (m, 2H, 2 CH), 4.95-5.16 (m, 6H, 2 NH , 2 OH).
2
2
2
Method for Separating Diastereoisomers of S-Containing Amino Acids by Recrystallization. A weighed portion
of methionine sulfoxide was recrystallized from methanol (40 mL, 80%). The compound obtained after recrystallization was
dissolved in water (10 mL). Methanol was added to make the solution 60, 75, 85, and 91% in methanol by addition to the
filtrate from each precipitation.
The following compounds were obtained by this method:
L-Methionine sulfoxide (5′), mp 178°C (dec.), [α]D20 +60° (c 2.0, H O). PMR spectrum (400 MHz, D O, δ, ppm):
2
2
2
2
.29-2.39 (m, 2H, CH CH), 2.74 (s, 3H, CH ), 3.00-3.14 (m, 2H, CH S), 3.86-3.92 (m, 1H, CH), 4.78 (s, 3H, NH , OH).
2 3 2 2
20
L-Methionine sulfoxide (5″), mp 238°C (dec.), [α]D −68° (c 7.3, H O). PMR spectrum (400 MHz, D O, δ, ppm):
2
2
.35-2.37 (m, 2H, CH CH), 2.75 (s, 3H, CH ), 3.00-3.15 (m, 2H, CH S), 4.04-4.08 (m, 1H, CH), 4.77 (s, 3H, NH , OH).
2
3
2
2
ACKNOWLEDGMENT
We thank V. P. Krasnov, Doctor of Chemical Sciences, Professor, Head of the Laboratory of Asymmetric Synthesis
of the I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, RAS, Ekaterinburg, for supplying the compounds.
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