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Conformationally Restricted Glutamic Acid Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2014 Conformationally restricted glutamic acid analogues: stereoisomers of 1-aminospiro[3.3]heptane-1,6-dicarboxylic acid Anton V. Chernykh, a, b Dmytro S. Radchenko, a, c Oleksandr O. Grygorenko, c Dmitriy M. Volochnyuk, b Svitlana V. Shishkina, d Oleg V. Shishkin d and Igor V. Komarov c, * a Enamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv 02660, Ukraine c Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine E-mail: [email protected] d STC “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Lenina ave., 61001 Kharkiv, Ukraine S1 Table of contents. 1. 1H NMR spectrum of the compound 8 S5 2. 13 C NMR spectrum of the compound 8 S6 3. 1H NMR spectrum of the compound 13 S7 4. 13 C NMR spectrum of the compound 13 S8 5. 31 P NMR spectrum of the compound 13 S9 6. 1H NMR spectrum of the compound 15 S10 7. 13 C NMR spectrum of the compound 15 S11 8. 1H NMR spectrum of the compound 9 S12 9. 13 C NMR spectrum of the compound 9 S13 10. 1H NMR spectrum of the compound 11a S14 11. 13 C NMR spectrum of the compound 11a S15 12. NOE spectrum of the compound 11a S16 13. HMBC spectrum of the compound 11a S17 14. 1H-1H COSY spectrum of the compound 11a S18 15. NOESY spectrum of the compound 11a S19 16. NOESY spectrum of the compound 11a (fragment) S20 17. 1H NMR spectrum of the compound 11b S21 18. 13 C NMR spectrum of the compound 11b S22 19. NOE spectrum of the compound 11b S23 20. 1H-1H COSY spectrum of the compound 11b S24 21. HMBC spectrum of the compound 11b S25 22. NOESY spectrum of the compound 11b S26 23. NOESY spectrum of the compound 11b (fragment) S27 24. 1H NMR spectrum of the compound 16a S28 25. 13 C NMR spectrum of the compound 16a S29 S2 26. 1H NMR spectrum of the compound 16b S30 27. 13 C NMR spectrum of the compound 16b S31 28. 1H NMR spectrum of the compound 16c S32 29. 13 C NMR spectrum of the compound 16c S33 30. 1H NMR spectrum of the compound 16d S34 31. 13 C NMR spectrum of the compound 16d S35 32. 1H NMR spectrum of the compound 1a ⋅HCl S36 33. 13 C NMR spectrum of the compound 1a ⋅HCl S37 34. 1H NMR spectrum of the compound 1b ⋅HCl S38 35. 13 C NMR spectrum of the compound 1b ⋅HCl S39 36. 1H NMR spectrum of the compound 1c ⋅HCl S40 37. 13 C NMR spectrum of the compound 1c ⋅HCl S41 38. 1H NMR spectrum of the compound 1d ⋅HCl S42 39. 13 C NMR spectrum of the compound 1d ⋅HCl S43 40. 1H NMR spectrum of the compound 18a S44 41. 13 C NMR spectrum of the compound 18a S45 42. 1H NMR spectrum of the compound 18b S46 43. 13 C NMR spectrum of the compound 18b S47 44. 1H NMR spectrum of the compound 18c S48 45. 13 C NMR spectrum of the compound 18c S49 46. 1H NMR spectrum of the compound 18d S50 47. 13 C NMR spectrum of the compound 18d S51 48. 13 C DEPT spectrum of the compound 18d S52 49. 1H NMR spectrum of the compound 19 c S53 50. 13 C NMR spectrum of the compound 19 c S54 51. Stereochemical assignments of 1a -d S55 S3 52. Table S1. Crystallographic data and experimental parameters S56 for the compound 13 and 18a-c 53. ORTEP diagrams of the compounds 18a–c S57 S4 1H NMR spectrum of the compound 8 S5 13С NMR spectrum of the compound 8 S6 1H NMR spectrum of the compound 13 S7 13С NMR spectrum of the compound 13 S8 31 P NMR spectrum of the compound 13 S9 1H NMR spectrum of the compound 15 S10 13C NMR spectrum of the compound 15 S11 1H NMR spectrum of the compound 9 S12 13С NMR spectrum of the compound 9 S13 1H NMR spectrum of the compound 11a S14 13C NMR spectrum of the compound 11a S15 NOE spectrum of the compound 11a S16 HSQC spectrum of the compound 11a S17 1H-1H COSY spectrum of the compound 11a S18 NOESY spectrum of the compound 11a S19 NOESY spectrum of the compound 11a (fragment) S20 1H NMR spectrum of the compound 11b S21 13C NMR spectrum of the compound 11b S22 NOE spectrum of the compound 11b S23 1H-1H COSY spectrum of the compound 11b S24 HSQC spectrum of the compound 11b S25 NOESY spectrum of the compound 11b S26 NOESY spectrum of the compound 11b (fragment) S27 1H NMR spectrum of the compound 16a S28 13C NMR spectrum of the compound 16a S29 1H NMR spectrum of the compound 16b S30 13C NMR spectrum of the compound 16b S31 1H NMR spectrum of the compound 16c S32 13C NMR spectrum of the compound 16c S33 1H NMR spectrum of the compound 16d S34 13C NMR spectrum of the compound 16d S35 1H NMR spectrum of the compound 1a ⋅HCl S36 13C NMR spectrum of the compound 1a ⋅HCl S37 1H NMR spectrum of the compound 1b⋅HCl S38 13C NMR spectrum of the compound 1b⋅HCl S39 1H NMR spectrum of the compound 1c⋅HCl S40 13C NMR spectrum of the compound 1c⋅HCl S41 1H NMR spectrum of the compound 1d⋅HCl S42 13C NMR spectrum of the compound 1d⋅HCl S43 1H NMR spectrum of the compound 18a S44 13C NMR spectrum of the compound 18a S45 1H NMR spectrum of the compound 18b S46 13C NMR spectrum of the compound 18b S47 1H NMR spectrum of the compound 18c S48 13C NMR spectrum of the compound 18c S49 1H NMR spectrum of the compound 18d S50 13C NMR spectrum of the compound 18d S51 13C DEPT spectrum of the compound 18d S52 1H NMR spectrum of the compound 19c S53 13C NMR spectrum of the compound 19c S54 Stereochemical assignments of 1a-d The stereochemical assignment of the final compounds 1a-d was done basing on several experiments: 1D- and 2D-NOESY for compounds 11a ,b (see above) and X-ray diffractional studies of three purposely synthesized compounds 18a -c. Before performing the NOE studies, we assigned the NMR signals in the spectra of 11a ,b using APT, HSQC, H,H-COSY experiments (see the spectra above). The H2 proton (which gives NMR signal at 3.15 ppm for 11a, 3.08 ppm for 11b ), assigned reliably by its correlation with the C2 in the HSQC (the only tertiary carbon atom, 32.8 ppm for 11a, 31.9 ppm for 11b) was irradiated; NOE effect was observed for the proton with the chemical shift 2.54 ppm for 11a and 2.19-2.34 ppm for 11b . At the same time, strong NOE correlation was observed in the 2D-NOESY spectra for H7 (1.97 ppm (11 а) and 2.11 ppm ( 11b)): with the signals H1b in 11a (2.33 ppm) and H3b in 11b (2.19-2.34 ppm). From these data we concluded that signals at 2.54 ppm ( 11 а) and 2.63-2.77 ppm ( 11b) correspond to Н1а and Н3а. Hence, the keto-ester 11a is the trans -isomer, because its H2 proton reveals strong NOE with Н1а and Н3а. Compound 11b is the cis -isomer, because its H2 proton shows strong NOE with Н1b and Н3b. The crystallographic data, experimental parameters and CCDB deposition numbers are listed in Table S1. ORTEP diagrams of the compounds 18a–c illustrate the absolute configuration of the stereocenters in these compounds. Ideally, X-Ray analysis of all the four derivatives 18a -d would give us enough information regarding the stereochemistry of 1a -d, because compounds 16a -d bear chiral auxiliary with the defined absolute configuration and transformed both into 1a -d and 18a -d without racemization at the stereocenters. However, compound 18d did not give crystals suitable for the X-Ray study. Its absolute stereoconfiguration was deduced using the following reasoning. Compound 18d is the only diastereomer of the four possible (the chiral auxiliary group was derived from the S-α-phenylglycinol for all the diastereomers); its absolute configuration at one of the stereocenter C2 (2 S) should be the same as in its precursor 11b , determined by 1D- and 2D-NOESY experiments. The other stereocenter C5 must have the stereoconfiguration reverse to that in its diastereomer 18c , thus, 5 S. S55 Table S1 Crystallographic data and experimental parameters for the compound 13 and 18a–c Parameter 13 18a 18b 18c a, Å 8.9199(4) 6.0940(5) 6.1255(6) 10.260(3) b, Å 18.9724(8) 15.418(2) 11.218(1) 5.820(2) c, Å 17.167(1) 17.637(2) 24.188(2) 14.060(4) α, deg 90.0 90.0 90.0 90.0 β, deg 100.522(5) 90.0 90.0 98.37(3) γ, deg 90.0 90.0 90.0 90.0 V, Å 3 2856.4(3) 1657.1(3) 1662.1(3) 830.6(5) T, K 293(2) 293(2) 293(2) 293(2) F(000) 1132 672 672 336 Crystal system Monoclinic Rhombic Rhombic Monoclinic Space group P21/n Р212121 Р212121 Р21 Z 2 4 4 2 µ, mm -1 0.307 0.089 0.089 0.089 3 dcalc , g/cm 1.256 1.264 1.260 1.261 2Θmax , deg 50 60 60 60 Reflection measured 19720 8562 13719 7469 Reflections independent 5018 4455 4755 4370 Rint 0.023 0.071 0.102 0.155 Reflections with F>4 σ(F) 3827 1524 1883 836 R1 0.098 0.048 0.055 0.066 wR 2 0.285 0.064 0.084 0.159 S 1.227 0.793 0.840 0.696 CCDC deposition number 962474 962475 962476 962477 S56 ORTEP diagrams of the compounds 18a–c 18a 18b 18c S57 .
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