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Original Articles

Synthesis of SE- and TE-Containing Amino Acids: Useful Probes for Structural Studies of Proteins

Pages 611-616 | Published online: 17 Mar 2008

REFERENCES AND NOTES

  • Salzmann , M. , Knaute , T. , Silks , L. A. , Müller , S. , Böck , A. and Senn , H. 1996 . “1 77 77Se-Labeled Amino Acids and Proteins.” . Second European Conference on Stable Isotope Aided NMR of Biomolecules in Frankfurt . 3-5 March 1996 , Germany. H Senn M Salzmann L A Silks S Müller A Böck and A Ross “1 77 77 77 2-Thioredoxin” Gordon Research Conference: Magnetic Resonance in Biology & Medicine Jan 26-31 1997 Ventura CA USA
  • Hendrickson W. A. Science , 254 , 51 ( 1991 ).
  • Boles J. O. Lebioda L. Dunlap R. B. Odom J. D. , SAAS Bull. Biochem. Biotechnol. , 8 , 29 ( 1995 ). J. O. Boles, K. Lewinski, M. G. Kunkle, M. Hatada, L. Lebioda, R. B. Dunlap and J. D. Odom, Acta Crystallogr., D, 51, 731 (1995). J. O. Boles, K. Lewinski, M. Kunkle, J. D. Odom, M. Hatada, R. B. Dunlap and L. Lebioda, Nat. Struct. Biol., 1, 283 (1994) .
  • Budisa N. Steipe B. Demange P. Eckerskorn C. Kellermann J. Huber R. , Eur. J. Biochem. , 230 , 788 ( 1995 ). N. Budisa, W. Kambrock, S. Steinbacher, A. Humm, L. Prade, T. Neuefeind, L. Moroder, R. Huber, J. Mol. Biol., 270, 616 (1997). A. Humm, E. Fritsche, S. Steinbacher, R. Huber R., EMBO J., 16, 3373 (1997). S. Steinbacher, S. Miller, U. Baxa, N. Budisa, A. Weintraub, R. Seckler, R. Huber, J. Mol. Biol., 267, 865 (1997) .
  • Stocking E. M. Schwarz J. N. Senn H. Salzmann M. M. Silks L. A. , J. Chem. Soc., Perkins Trans. 1 , 2443 ( 1997 ).
  • For a different 77Se chemical shift reported for Se-Cys see, Besse D. Siedler F. Diercks T. Kessler H. Moroder L. Angewandte Chem. , 36 , 883 ( 1997 ). For leading references on the use of 77Se NMR spectroscopy see the following. L. A. Silks, R. B. Dunlap and J. D. Odom, J. Am. Chem. Soc., 112, 4979, (1990). L. A. Silks, J. Peng, J. D. Odom and R. B. Dunlap, J. Org. Chem., 56, 6733 (1991). J. Peng, M. E. Barr, D. A. Ashburn, J. D. Odom, R. B. Dunlap and L. A. Silks, J. Org. Chem., 59, 4977 (1994). J. Peng, J. D. Odom, R. B. Dunlap and L. A. Silks, Tetrahedron: Asymmetry, 5, 1627 (1994). R. Wu, J. D. Odom, R. B. Dunlap and L. A. Silks, Tetrahedron: Asymmetry, 6, 833 (1995). J. Peng, M. E. Barr, D. A. Ashburn, L. Lebioda, A. R. Garber, R. A. Martinez, J. D. Odom, R. B. Dunlap and L. A. Silks J. Org. Chem., 60, 5540 (1995). R. Wu, G. Hernandez, J. D. Odom, R. B. Dunlap, L. A. Silks J. Chem. Soc. Chem. Commun., 10, 1125 (1996). R. Wu, J. D. Odom, R. B. Dunlap, L. A. Silks, L. A. Spectroscopy, 11, 37 (1996) .
  • Silks L. A. Boles J. O. Modi B. P. Dunlap R. B. Odom J. D. , Synthetic Commun. , 20 , 1555 , ( 1990 ).
  • Bong G. Lynn D. G. J. Org. Chem. , 55 , 4763 ( 1990 ).
  • Karnbrock W. Weyher E. Budisa N. Huber R. Moroder L. , J. Am. Chem. Soc. V. 118 , 913 ( 1996 ). D. Besse, N. Budisa, W. Karnbrock, C. Minks, H. Musiol, S. Pegoraro, F. Siedler, E. Weyher, L. Moroder, Biol. Chem., 378, 211 (1997) .
  • Typical procedure. Caution: methyl tellurol, methyl telluride, and dimethyl ditelluride are noxious, volatile, and probably toxic materials. All manipulations must be carried out in a high velocity hood and protective clothing and gloves should be worn. The HSL was added to a 250 mL three-necked round bottom flask which was fitted with two rubber septa and a magnetic stir bar. The flask was directly attached to a glass vacuum manifold. Methanol was added (100 mL) and the system was then pumped down to a constant pressure of 0.030 Torr. To this was added a THF solution of methyltellurolate (1.80 equivalents). The resulting yellow solution was warmed to room temperature. The solvents were then slowly removed over a 2-4 hour period. During this time ice formed on the outside surface of the round bottom flask. The resulting brown foam was taken up in 20 mL of water. The mixture was stirred for 1h under a light vacuum (enough to chill the flask). The cooled aqueous mixture was then filtered through prewashed and hydrated Celite (more than one filtration may be required). The Celite was washed one time with a minimal amount of cold water. The solution was then acidified with solid citric acid monohydrate. The solids which formed were collected and then dried. All compounds have been characterized spectrally (1H, 13C, and 125Te NMR, MS and/or elemental analysis). We have supplied (l)-Te-Met to accredited researchers since 1990 .

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