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1 D-glucose based syntheses of -hydroxy derivatives of L-glutamic acid, L-glutamine, L-proline and a dihydroxy pyrrolidine alkaloid K. S. Ajish Kumar*, Subrata Chattopadhyay Bio-organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai- 400085 Email: [email protected] Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2015

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Page 1: Bio-organic Division, Bhabha Atomic Research Centre ... · 1 D-glucose based syntheses of -hydroxy derivatives of L-glutamic acid, L-glutamine, L-proline and a dihydroxy pyrrolidine

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D-glucose based syntheses of -hydroxy derivatives of L-glutamic acid, L-glutamine, L-proline and a dihydroxy pyrrolidine alkaloid

K. S. Ajish Kumar*, Subrata Chattopadhyay

Bio-organic Division, Bhabha Atomic Research Centre,

Trombay, Mumbai- 400085

Email: [email protected]

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015

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Content

s.no Title Page no.

1 1H NMR spectrum of 4 6

2 13C NMR spectrum of 4 7

3 1H NMR spectrum of 5 8

4 13C NMR spectrum of 5 9

5 1H NMR spectrum of 6 10

6 13C NMR spectrum of 6 11

7 ESI-MS spectrum of 6 12

8 1H NMR spectrum of 7 13

9 13C NMR spectrum of 7 14

10 1H NMR spectrum of 8 15

11 13C NMR spectrum of 8 16

12 1H NMR spectrum of 9 17

13 13C NMR spectrum of 9 18

14 1H NMR spectrum of 10 19

15 13C NMR spectrum of 10 20

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16 1H NMR spectrum of 11 21

17 13C NMR spectrum of 11 22

18 1H NMR spectrum of 12 23

19 13C NMR spectrum of 12 24

20 ESI-MS spectrum of 12 25

21 1H NMR spectrum of 13 26

22 13C NMR spectrum of 13 27

22 1H NMR spectrum of 14 28

23 13C NMR spectrum of 14 29

24 ESI-MS spectrum of 14 30

25 1H NMR spectrum of 1a 31

26 13C NMR spectrum of 1a 32

27 ESI-MS spectrum of 1a 33

28 1H NMR spectrum of 15 34

29 13C NMR spectrum of 15 35

30 ESI-MS spectrum of 15 36

31 1H NMR spectrum of 16 37

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32 13C NMR spectrum of 16 38

33 1H NMR spectrum of 17 39

34 13C NMR spectrum of 17 40

35 ESI-MS spectrum of 17 41

36 1H NMR spectrum of 18 42

37 13C NMR spectrum of 18 43

38 ESI-MS spectrum of 18 44

39 1H NMR spectrum of 19 45

40 13C NMR spectrum of 19 46

41 ESI-MS spectrum of 19 47

42 1H NMR spectrum of 20 48

43 13C NMR spectrum of 20 49

44 1H NMR spectrum of 1b 50

45 13C NMR spectrum of 1b 51

46 ESI-MS spectrum of 1b 52

47 1H NMR spectrum of 21 53

48 13C NMR spectrum of 21 54

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49 1H NMR spectrum of 22 55

50 13C NMR spectrum of 22 56

51 ESI-MS spectrum of 22 57

52 1H NMR spectrum of 23 58

53 13C NMR spectrum of 23 59

54 ESI-MS spectrum of 23 60

55 1H NMR spectrum of 24 61

56 13C NMR spectrum of 24 62

57 ESI-MS spectrum of 24 63

58 1H NMR spectrum of 1c 64

59 13C NMR spectrum of 1c 65

60 1H NMR spectrum of 2 66

61 13C NMR spectrum of 2 67

62 COSY spectrum of 2 68

63 HMQC spectrum of 2 69

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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Note: The BBI and TXI probe on which 13C NMR (126 MHz) was done, is not optimized for the detection of the 13C nucleus, being an inverse probe, it is optimized for 1H detection, and therefore for weak samples a small hump appears.

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