Resolution of Enantiomeric Mixtures of Amino Acids and Derivatives

The measurement of specific rotation is a common and accepted method for evaluating the enantiomeric

Table 16 hRF values of 15 amino acids on silica gel impregnated with Zn, Cd and Hg salts

ABCDEFGHI J

Table 16 hRF values of 15 amino acids on silica gel impregnated with Zn, Cd and Hg salts

ABCDEFGHI J

Thr

25

55

42

41T

35

36

42

33

50

40

Ser

12

38

39

28T

32

29

31T

15

40

31T

Gly

10

35

29

23T

28

25

28

16

35

27T

Lys

03

13

07

05

51

08

05

04

10

05

Ala

30

48

40

31

38

36

38

20

5

35

Tyr

60

60

52

50

48

45

51

62

55

56

Ile

55

67

56

52

50

48

54

50

60

53

Leu

50

65

55

55

52

50

56

47

64

55

Cys

00

00

00

00

00

00

00

00

00

00

Met

45

62

48

48

48

42

48

39

54

45

Glu

18T

43

38

36T

34

27

38T

18

36

34T

Try

57

60

53

51

51

44

54

45

60

47

Phe

54

67

57

55

55

46

57

58

68

52

Val

50

63

45

50

52

42

56

47

57

45

Arg

07

19

13

13

09

11

11

10

15

08

Solvent, butyl acetate-methanol-acetic acid-pyridine (20 : 20 : 5 : 5, v/v). Developing time, 30 min. Detection limit, 10~4 mol L~1. Solvent front, 10 cm. A, plain silica gel; B, C, D, 0.5%, 0.2%, 0.1% Zn2+C-impregnated, respectively; E, F, G. 0.5, 0.2, 0.1% Cd2+-impregnated, respectively; H, I, J, 0.5, 0.2, 0.1% Hg2+, respectively. T = tailing.

purity of chiral compounds. The determination of enantiomeric excess (ee) values is influenced by the presence of impurities and changes in concentration, solvent and temperature, and requires the [a]D value for the pure enantiomer. The availability of a reliable optically pure standard depends on the analytical method by which it had been resolved from the enan-tiomeric or racemic mixture of the compound in question. Though TLC provides a direct method for resolution and analytical control of enantiomeric purity, there are few reports on TLC separation of enantiomers.

In general, the following approaches for the resolution of enantiomers have been used.

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