Synthesis of all possible regioisomers of myo-inositol pentakisphosphate

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 17, 1996, Pages 2039-2042

  Chung, Sung Kee ^a   Chang, Young Tae ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

INOSITOL PENTAKISPHOSPHATE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030567871     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00371-X     Document Type: Article

References (17)

1. a) Shears, S. B. Biochem. J. 1989, 260, 313-324;
2. b) Berridge, M. J. Nature (London) 1993, 361, 315-325.
3. Irvine, R. F.; Cullen, P. J. Current Biology 1993, 3, 540-543.
4. Hughes, P. J.; Shears, S. B. J. Biol. Chem. 1990, 265, 9869-9875.
5. Donie, F.; Reiser, G. Biochem. J., 1991, 275, 453-457.
6. Angyal, S. J.; Russell, A. F. Aust. J. Chem. 1968, 21, 391-404.
7. Ozaki, S.; Koga, Y.; Ling, L.; Watanabe, Y.; Kimura, Y.; Hirata, M. Bull. Chem. Soc. Jpn. 1994, 67, 1058-1063.
8. a) Chung, S. K.; Chang, Y. T. J. Chem. Soc., Chem. Commun. 1995, 11-12;
9. b) Chung, S. K.; Chang, Y. T.; Sohn, K. H. J. Chem. Soc., Chem. Commun. 1996, 163-164.
10. Chung, S. K.; Chang, Y. T. J. Chem. Soc., Chem. Commun. 1995, 13-14.
11. 2 TLC (ethyl acetate-hexane 2:1, three times) is 5c (0.10), 5a (0.15), 5d (0.25), 5c' (0.3). All isomers are crystalline solids and their melting points are 5c (183-184 °C), 5a (209-211 °C), 5d (205-208 °C), 5c' (158-161 °C).
12. Andersch, P; Schneider, M. P. Tetrahedron: Asymmetry 1993, 4, 2135-2138.
13. Billington, D. C.; Baker, R.; Kulagowski, J. J.; Mawer, I.; Vacca, J. P.; deSolms, S. J.; Huff, J. R. J. Chem. Soc., Perkin Trans. 1, 1989, 1423-1429.
14. 3OD) for the ring protons in IBz (1) are as follows. 1a. 219-220 °C; δ 3.26 (t, J = 9.1 Hz, 1H, H-5), 3.41 (dd, J = 2.7, 9.7 Hz, 1H, H-3), 3.60 (dd, J = 9.1, 9.7 Hz, 1H, H-4), 3.91 (dd, J = 9.1, 10.2 Hz, 1H, H-6), 4.10 (t, J = 2.7 Hz, 1H, H-2), 4.80 (dd, J = 2.7, 10.2 Hz, 1H, H-1). 1b. 240-242 °C; δ 3.30 (t, J = 8.9 Hz, 1H, H-5), 3.66 (dd, J = 2.6, 9.7 Hz, 2H, H-1 & H-3), 3.73 (dd, J = 8.9, 9.7 Hz, 2H, H-4 & H-6), 5.69 (t, J = 2.6 Hz, 1H, H-2). lc. 208-210 °C; δ 3.46 (dd, J = 2.7, 9.7 Hz, 1H, H-1), 3.49 (t, J = 9.5 Hz, 1H, H-5), 3.71 (dd, J = 2.7, 10.0 Hz, 1H, H-3), 3.78 (dd, J = 9.5, 9.7 Hz, 1H, H-6), 4.04 (t, J = 2.7 Hz, 1H, H-2), 5.45 (app t, J = 9.8 Hz, 1H, H-4). 1d. 238-240 °C; δ 3.52 (dd, J = 2.8, 9.8 Hz, 2H, H-1 & H-3), 3.91 (app t, J = 9.7 Hz, 2H, H-4 & H-6), 4.05 (t, J = 2.8 Hz, 1H, H-2), 5.04 (t, J = 9.6 Hz, 1H, H-5).
15. 4 as the reference standard). 2a. δ 0.26 (2P), 0.46, 0.82, 1.06. 2b. δ 0.46 (2P), 0.61 (3P). 2c. δ -0.11, 0.08, 0.67, 1.32 (2P). 2d. δ -0.18, 0.61 (2P), 1.45 (2P).
16. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M.-C. Tetraheron Lett. 1977, 18, 155-158.
17. 4 as the reference standard). 3a. δ 6.07, 6.20, 6.54, 6.77, 7.22. 3b. δ 5.98 (2P), 6.35, 6.83 (2P). 3c. δ 6.05 (2P), 6.75, 7.13, 7.27. 3d. δ 6.00, 6.92 (2P), 7.90 (2P).