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The exclusive exo cycloaddition might be attributed to its putative transition state conformation 4 which is sterically more favorable than that of the endo transition state.
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38
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85033862260
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note
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2 was purified prior to use (see the Experimental Section). We thank Professor M. Mandai, Okayama University of Science, for informing us of this purification procedure.
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39
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85033860409
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Methylation of the primary alcohol using NaH/MeI was not satisfactory since a considerable amount of N-methylated byproduct was also obtained.
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Prepared from (2S,1′S,2′R)-n-(tert-butoxycarbonyl)-2-[(ethoxycarbonyl)cyclopropyl] glycinol. (a) Shimamoto, K.; Ohfune, Y. New routes to the synthesis of cis-α-(carboxycyclopropyl)glycines from L-glutamic acid. Conformationally constrained analogues of the excitatory neurotransmitter L-glutamic acid. Tetrahedron Lett. 1980, 30, 3803-3894. (b) See ref 8b.
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85033859092
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note
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1H NMR.
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60
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85033846948
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note
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The C-2H of CCG-IV was observed as a broad signal at pH 9-11 where slow exchange of the nonprotonated and the protonated amino group might affect the broadening of the signal at C-2H.
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61
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85033867094
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note
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2H-1′H values of trans-MCG-III and -IV (pH > 8-0) and cis-MCG-IV (pH > 9) could not be obtained because of the broadening signals of both 2H and 1′H.
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62
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For an example of molecular mechanics calculation of glutamate analogs, see: Bridges, R. J.; Lovering, F. E.; Humphrey, J. M.; Stanley, M. S.; Blakely, T. N.; Cristofaro, M. F.; Chamberlin, A. R. Conformationally restricted inhibitors of the high affinity L-glutamate transporter. Bioorg. Med. Chem. Lett. 1993, 3, 115-121.
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63
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85033845159
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note
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The rotation of both the carboxylates of CCGs did not affect the minimization.
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64
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85033853931
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note
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Calculations of cis-MCG-I and -IV were performed by rotating the C2-C1′ bond and the two bonds of the C3′ methoxymethyl group (in 60° increments) and provided 32 and 23 minimized structures, respectively. Among them, the existence ratio of the H-C2-C1′-H antiperiplanar type conformers were 96.6% for cis-MCG-I and 99.3% for cis-MCG-IV. These results were in good agreement with those of Me-substituted CCGs.
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65
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85033856692
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note
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We thank Dr. N. Hamanaka, Director, Minase Research Institute of Ono Pharmaceutical Co. Ltd., for X-ray crystallographic analysis of CCGs. We could not prepare crystals of CCG-I suitable for X-ray crystallographic analysis because this compound formed fine powders under numerous recrystallization conditions.
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66
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0000646010
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A short hydrogen bond between near identical carboxyl group in the α modification of L-glutamic acid
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85033837549
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2c,5b,10d,19 although at high concentrations this compound binds to NMDA receptors. We believe that the extended partial structure of DCG-IV also contributes to its potent activity to mGluRs.
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72
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85033862695
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note
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The rms value of E and CCG-I (antiperiplanar conformer) was 0.117 Å.
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73
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A conformationally constrained competitive inhibitor of the sodium-dependent glutamate transporter in forebrain synaptosomes: L-anti-endo-3,4-methanopyrrolidine dicarboxylate
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CMP-II and -III have already been synthesized and characterized as L-syn-exo-MPDC and L-anti-endo-MPDC, respectively. Bridges, R. J.; Levering, F. E.; Koch, H.; Cotman, C. W.; Chamberlin, A. R. A conformationally constrained competitive inhibitor of the sodium-dependent glutamate transporter in forebrain synaptosomes: L-anti-endo-3,4-methanopyrrolidine dicarboxylate. Neuroscience Lett. 1994, 174, 193-197.
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85033865271
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note
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2O).
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75
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85033868469
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note
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Unpublished observations using electrophysiological method in the new born rat isolated spinal cord. There would be many reasons why CMPs are inactive to the receptors (e.g., steric hindrance, transport difficulties, and no flexibility to change its conformation). These factors could not be ruled out by the present studies.
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76
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85033841560
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The rms values of I and L with CCG-IV (antiperiplanar conformer) were 0.078 and 0.280 Å, respectively.
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84
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85033843708
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