Reagents for Bioorganic Synthesis. 6. The Design and Synthesis of Two Novel Polyfunctional Organic Reagents for Biomacromolecular Modification

References and Footnotes

• Bertha , C. M. , Hosmane , R. S. , Zhang , H. and Hosmane , N. S. 1992 . J. Org. Chem. , 57 : 5868 – 5873 . and the references cited therein
   Google Scholar
• Bertha , C. M. and Hosmane , R. S. 1992 . Tetrahedron Lett. , 33 : 3425 – 3428 .
   Google Scholar
• Hosmane , R. S. , Bertha , C. M. , Siriwardane , U. and Hosmane , N. S. 1990 . J. Org. Chem. , 55 : 5206 – 5216 .
   Google Scholar
• Hosmane , R. S. and Bertha , C. M. 1990 . Biochem. Biophys. Res. Commun. , 166 : 567 – 573 .
   PubMed Web of Science ®Google Scholar
• Hosmane , R. S. and Bertha , C. M. 1990 . Synth. Commun. , 20 : 2921 – 2935 .
   Web of Science ®Google Scholar
• Hosmane , R. S. and Bertha , C. M. 1988 . Tetrahedron Lett. , 29 : 5847 – 5850 .
   Web of Science ®Google Scholar
• Winslow , R. M. 1992 . “Hemoglobin- based Red Cell Substitutes” Baltimore : The Johns Hopkins University Press . For leading reviews, monographs, and news & comments, see: (a) (b) Moffat, A.S., “Three Li'l Pigs and the Hunt for Blood Substitutes”, Science 253, 32–34 (1991). (c) Pool, R., “Slow Going for Blood Substitutes”, Science 250, 1655–56 (1990). (d) Advances in Blood Substitutes Research; Bolin, R.B., Beyer, R.P. and Nemo, G.J., Eds.; Alan R. Liss: New York, 1983. (e) Miller, I.F., “Synthetic Blood Substitutes: Where Are We and Where Do We Go from Here?”, CRC Crit. Rev. Bioeng. 149–177 (1978)
   Google Scholar
• Bunn , H. F. , Esham , W. T. and Bull , R. W. 1969 . J. Exp. Med. , 129 : 909 – 924 .
   PubMed Web of Science ®Google Scholar
• DeVenuto , F. and Zegna , A. 1983 . J. Surg. Res. , 34 : 205 (b) Hopwood, D., Allen, C.R. and McCabe, M., Histochem. J. 2, 137 (1970)
   PubMed Web of Science ®Google Scholar
• Mok , W. , Chen , D.-E. and Mazur , A. 1975 . Fed. Proc. , 34 : 1458
   PubMedGoogle Scholar
• Larsen , R. W. , Chavez , M. D. , Ondrias , M. R. , Courtney , S. H. , Friedman , J. M. , Lin , M. J. and Hirsch , R. E. 1990 . J. Biol. Chem. , 265 : 4449 – 4454 . (b) Vandegriff, K.D., Le Tellier, Y.C., Winslow, R.M., Rohlfs, R.J. and Olson, J. S., J. Biol. Chem. 266, 17049–17059 (1991). (c) Snyder, S.R., Welty, E.V., Walder, R.Y., Williams, L.A. and Walder, J.A., Proc. Natl. Acad. Sci. USA 84, 7280 (1987). (d) Chatterjee, R., Welty, E.V., Walder, R.Y., Pruitt, S.L., Rogers, P.H., Arnone, A. and Walder, J.A., J. Biol. Chem. 261, 9929 (1986). (e) Vandegriff, K. D., Medina, F., Marini, M.A. and Winslow, R.M., J. Biol. Chem. 264, 17824–33 (1989)
   PubMedGoogle Scholar
• Walder , J. A. , Walder , R. Y. and Arnone , A. 1980 . J. Mol. Biol. , 141 : 195 (b) Shibayama, N., Imai, K., Hirata, H., Hiraiwa, H., Morimoto, H. and Saigo, S., Biochemistry 30, 8158–8165 (1991)
   PubMed Web of Science ®Google Scholar
• Bucci , E. , Razynska , A. , Urbaitis , B. and Fronticelli , C. 1989 . J. Biol. Chem. , 264 : 6191 – 6195 . (b) Fronticelli, C., Sato, T., Orth, C. and Bucci, E., Biochem. Biophys. Acta 874, 76 (1986)
   PubMed Web of Science ®Google Scholar
• Benesch , R. E. and Kwong , S. 1988 . Biochem. Biophys. Res. Commun. , 156 : 9 – 14 .
   PubMed Web of Science ®Google Scholar
• Benesch , R. E. and Kwong , S. 1991 . J. of Protein Chemistry , 10 : 503 – 510 . (b) Benesch, R.E. and Kwong, S.J. Biol. Chem. 256, 14881–14885 (1990)
   PubMedGoogle Scholar
• Manning , L. R. , Morgan , S. , Beavis , R. C. , Chait , B. T. , Manning , J. M. , Hess , R. , Cross , M. , Currell , D. L. , Marini , MA and Winslow , R. M. 1991 . Proc. Natl. Acad. Sci. USA , 88 : 3329 – 3333 . (d) Kavanaugh, M.P., Shih, D.T.-B. and Jones, R.T., Biochemistry 27, 1804–1808 (1988)
   PubMed Web of Science ®Google Scholar
• Fermi , G. 1975 . J. Mol. Biol. , 97 : 237 – 256 . These values come from single-crystal X-ray diffraction studies on deoxy and oxy Hb: (a) (b) Shaanan, B., J. Mol. Biol. 171, 31–59 (1983). (c) Fermi, G., Perutz, M.F., Shaanan, B. and Fourme, R., J. Mol. Biol. 175, 159–174 (1984)
   PubMed Web of Science ®Google Scholar
• 1988 . The distances of reagents 1 and 2 were estimated by energy minimization utilizing ALCHEMY II“, force field molecular modeling software by Tripos Associates, St. Louis, Missouri
   Google Scholar
• Miyashita , N. , Yoshikoshi , A. and Grieco , P. A. 1977 . J. Org. Chem. , 42 : 3772 – 3774 . For protection and deprotection of hydroxyl groups with THP groups see
   Web of Science ®Google Scholar
• Bryan , D. B. , Hall , R. F. , Holden , K. G. , Huffman , W. F. and Gleason , J. G. 1977 . J. Am. Chem. Soc. , 99 : 2353 – 2355 . See, for example
   PubMed Web of Science ®Google Scholar
• Hamada , Y. , Shibata , M. , Sugiura , T. , Kato , S. and Shioiri , T. 1987 . J. Org. Chem. , 52 : 1252 For a recent application of this method, see
   Web of Science ®Google Scholar
• Kakis , F. J. , Fetizon , M. , Douchkine , N. , Golfier , M. , Mourgues , P. and Prange , T. 1974 . J. Org. Chem. , 39 : 523 – 533 . and the references therein
   Google Scholar
• Piancatelli , G. , Scettri , A. and D'Auria , M. 1982 . Synthesis , : 245 – 258 . For a review see
   Web of Science ®Google Scholar
• Fatiada , A. J. 1976 . Synthesis , : 133 – 167 . For a review, see 65–104 and
   Google Scholar
• Pfitzner , K. E. and Moffatt , J. G. 1965 . J. Am. Chem. Soc. , 87 : 5661 – 5678 . Also see reviews on activated DMSO oxidations (a) Mancuso, A.J. and Swern, D., Synthesis, 165–185 (1981), and. (b) Tidwell, T.T., Synthesis, 857–870 (1990)
   Web of Science ®Google Scholar
• Olovsson , I. and Jönsson , P.-G. 1976 . The Hydrogen Bond II. Structure and Spectroscopy Edited by: Schuster , P. , Zundel , G. and Sandorfy , C. 402 New York : North-Holland Pub. Co. .
   Google Scholar
• Weast , R. C. , ed. 1984 . Handbook of Chemistry and Physics, , 65th ed. F-166 – F-167 . Boca Raton , Florida : CRC .
   Google Scholar
• Still , W. C. , Kahn , M. and Mitra , A. 1978 . J. Org. Chem. , 43 : 2923 – 2925 .
   Web of Science ®Google Scholar
• The QUANTATM/CHARMmTM software package is available from Molecular Simulations, Inc., Boston, MA
   Google Scholar
• X-ray coordinates for the modeling were from reference 17c
   Google Scholar
• Taschner , E. , Biernat , J. F. , Rzeszotarska , B. and Wasielewski , C. 1961 . Liebigs Ann. Chem. , 646 : 123 – 124 . (b) Taschner, E., Wasielewski, C. and Biernat, J.F., Liebigs Ann. Chem. 646, 119–122 (1961)
   Google Scholar
• Olah , G. A. , Narang , S. C. , Gupta , B. G.B. and Malhotra , R. 1979 . Angew. Chem. Int. Ed. Engl. , 18 : 612 – 614 .
   Web of Science ®Google Scholar
• Sheldrick , G. M. 1990 . SHELXTL-Plus USA : Siemens Analytical X-Ray Instruments Inc. .
   Google Scholar
• 1974 . International Tables for X-ray Crystallography, Vol. IV, Birmingham: Kynock Press
   Google Scholar