Toluene-dioxygenase-mediated cis-dihydroxylation of aromatics in enantioselective synthesis. Iterative glycoconjugate coupling strategy and combinatorial design for the synthesis of oligomers of nor-saccharides, inositols and pseudosugars with interesting molecular porperties

Synthesis

Volumn , Issue 7, 1996, Pages 897-911

  Hudlicky, Tomas ^{a,c,d,e,f,g,h,i}   Abboud, Khalil A ^a   Entwistle, David A ^a   Fan, Rulin ^a   Maurya, Rakesh ^a   Thorpe, Andrew J ^a   Bolonick, Joel ^b   Myers, Brian ^a  

^a University of Florida ^*  (United States)

^b NZYM Inc   (United States)

^c Virginia Tech ^*

^d VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^e RICE UNIVERSITY   (United States)

^f UNIVERSITY OF GENEVA   (Switzerland)

^g ILLINOIS INSTITUTE OF TECHNOLOGY   (United States)

^h UNIVERSITY OF FLORIDA   (United States)

ⁱ UNIVERSIDAD DE MONTEVIDEO   (Uruguay)

Author keywords

biooxidation; calcium chelation; helical structure; inositol conjugates; toluene dioxygenase

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLYCOCONJUGATE; INOSITOL DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029929189     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4440     Document Type: Article

References (76)

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32. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
33. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
34. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
35. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
36. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
37. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
38. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
39. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
40. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
41. For recent applications describing the application of cyclo-3,5-diene-cis-1,2-diols in the synthesis of cyclitols and aminocyclitols see: a) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995. b) Johnson, C. R.; Ple, P. A.; Su, Lu.; Heeg, M. J.; Adams, J. P. Synlett. 1992, 388. c) Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006. d) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379. e) Carless, H. A. J.; Malik, S. S. Tetrahedron Asymmetry 1992, 3, 1135. f) Carless, H. A. J.; Busia, K. Carbohydr Res 1992, 234, 207. g) Carless, H. A. J.; J. Chem. Soc., Chem. Commun. 1992, 234. h) Carless, H. A. J.; Oak, O. Z.; J. Chem. Soc., Chem. Commun. 1991, 61. i) Carless, H. A. J.; Busia, K. Tetrahedron Lett 1990, 31, 3449. j) Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 1719.
42. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
43. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
44. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
45. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
46. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
47. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
48. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
49. For reviews on the use of cyclohexa-3,5-diene-cis-1,2-diols in organic synthesis see: a) Hudlicky, T.; Reed, J. W., In Advances in Asymmetric Synthesis; Hassner, Ed.; JAI Press: Greenwich, CT, 1995, 1, p271. b) Carless, H. A. J.: Tetrahedron Asymmetry 1992, 3, 795. c) Sheldrake, G. N. In Chirality in Industry; Collins, A. N.; d) Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992; p 127. e) Brown, S. M.; Hudlicky, T.; In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1992, p 113. f) Widdowson, D. A.; Ribbons, D. A.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3. g) Hudlickly, T. In Green Chemistry; Anastas, P. T.; Williamson, T. C.; Eds.; ACS Symposium Series, Vol. 626; ACS: Washington D. C.; 1966, p 180. h) Hudlicky, T. Chem. Rev. 1996, 96, 3.
50. Diols derived from chloro-, bromo-, cyano-, iodobenzene and naphthalene are comercially available from Eastman Fine Chemicals, Rochester, NY and from Genecor International Inc., South San Francisco.
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66. The iodo diol is made by whole cell bioxidation of iodobenzene with Pseudomonas putida 39D and is also commercially available from Eastman Fine Chemicals.
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