СТРАТЕГІЯ ТА ОТРиМАННЯ ДЕЯКИХ СИНТЕТИЧНИХ БЛОКІВ ДЛЯ СИНТЕЗУ РОЗГАЛУЖЕНИХ ОЛІГОСАХАРИДІВ

V. A. Bacherikov

Анотація


У статті обговорюються декілька сучасних дизайнерських рішень для планування синтезу разгалудженних олігосахаридів із застосуванням захисних функціональних груп різної реакційної здатності. Був представлений синтетичний план у якому застосовані такі захисні групи як ацетіл (Ac), бензіл (Bn), 2-нафтіл (2-Naph), п-метоксібензіл (PMB) і п-хлорбензіл (p-ClBn) та які у подальшому можуть бути селективно видалені з високим
видобутком. Описано методи синтезу деяких перспективних синтетичних блоків призначених для отримання відповідних розгалужених олігопохідних.

Ключові слова


синтетичні блоки, захищені моносахариди, β-(1,3)-D-глюкани, синтез

Повний текст:

PDF (English)

Посилання


Varki A. Biological roles of oligosaccharides: all of the theories are correct // Glycobiology. – 1993. – Т. 3, № 2. – C. 97-130. http://dx.doi.org/10.1093/glycob/3.2.97

Lehninger A.L.N., D.L.; Cox, M.M. Principles of Biochemistry. 2nd Ed. — N.Y. : worth Publishers Inc., 2000.

Phillips M.L., Nudelman E., Gaeta F.C., Perez M., Singhal A.K., Hakomori S., Paulson J.C. ELAM-1 mediates cell adhesion by recognition of a carbohydrate ligand, sialyl-Lex // Science (New York, N.Y.). – 1990. – Т. 250, № 4984. – C. 1130-1132. http://dx.doi.org/10.1126/science.1701274

Lasky L.A. Selectins: interpreters of cell-specific carbohydrate information during inflammation // Science (New York, N.Y.). – 1992. – Т. 258, № 5084. – C. 964-969. http://dx.doi.org/10.1126/science.1439808

wong C.H. Carbohydrate-based Drug Discovery. : wiley, 2006.

Hurtley S., Service R., Szuromi P. Cinderella’s Coach Is Ready // Science (New York, N.Y.). – 2001. – Т. 291, № 5512. – C. 2337. http://dx.doi.org/10.1126/science.291.5512.2337

Spohr U., Lemieux R.U. Synthetic, conformational, and immunochemical studies of modified Lewis b and Y human blood-group determinants to serve as probes for the combining site of the lectin IV of Griffonia simplicifolia // Carbohydrate Res. – 1988. – Т. 174,–C.211-237. http://dx.doi.org/10.1016/0008-6215(88)85093-6

Cipolla L., Peri F., Airoldi C. Glycoconjugates in cancer therapy // Anticancer Agents Med. Chem. – 2008. – Т. 8, № 1. – C. 92-121. http://dx.doi.org/10.2174/187152008783330815

Levy D.E., Tang P.C., Musser J.H. Chapter 22. Cell Adhesion and Carbohydrates // Annual Reports in Medicinal Chemistry Т. Volume 29. James A.B. : Academic Press, 1994. — C. 215-224.

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Davis A.P., wareham R.S. Carbohydrate Recognition through Noncovalent Interactions: A Challenge for Biomimetic and Supramolecular Chemistry // Angew. Chem. Int. Ed. Engl. – 1999. – Т. 38, № 20. – C. 2978-2996. http://dx.doi.org/10.1002/(sici)1521-3773(19991018)38:20<2978::aid-anie2978>3.0.co;2-p

Mazik M. Molecular recognition of carbohydrates by acyclic receptors employing noncovalent interactions // Chem. Soc. Rev. – 2009. – Т. 38, № 4. – C. 935-956. http://dx.doi.org/10.1039/b710910p

Audette G.F., Delbaere L.T., Xiang J. Mapping protein: carbohydrate interactions // Curr. Protein Pept. Sci. – 2003. – Т. 4, № 1. – C. 11-20. http://dx.doi.org/10.2174/1389203033380322

G. Davis B. Recent developments in glycoconjugates // J. Chem. Soc., Perkin Trans. 1. – 1999. – № 22. – C. 3215-3237. http://dx.doi.org/10.1039/a809773i

Randolph J.T., Danishefsky S.J. Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: the first synthesis of a complex saponin // J. Amer. Chem. Soc. – 1993. – Т. 115, № 18. – C. 8473-8474.

Danishefsky S.J., Bilodeau M.T. Glycals in Organic Synthesis: The Evolution of Comprehensive Strategies for the Assembly of Oligosaccharides and Glycoconjugates of Biological Consequence // Angew. Chem. Int. Ed. Engl. – 1996. – Т. 35, № 13-14. – C. 1380-1419. http://dx.doi.org/10.1002/anie.199613801

Hsu C.-H., Hung S.-C., wu C.-Y., wong C.-H. Toward Automated Oligosaccharide Synthesis // Angew. Chem. Int. Ed. Engl. – 2011. – Т. 50, № 50. – C. 11872-11923. http://dx.doi.org/10.1002/anie.201100125

Yamada H., Harada T., Takahashi T. Synthesis of An Elicitor-Active Hexaglucoside Analog by a One-Pot, Two-Step Glycosidation Procedure // J. Amer. Chem. Soc. – 1994. – Т. 116, № 17. – C. 7919-7920. http://dx.doi.org/10.1021/ja00096a068

Raghavan S., Kahne D. A one step synthesis of the ciclamycin trisaccharide // J. Amer. Chem. Soc. – 1993. – Т. 115, № 4. – C. 1580-1581. http://dx.doi.org/10.1021/ja00057a056

Ley S.V., Priepke H.w.M. A Facile One-Pot Synthesis of a Trisaccharide Unit from the Common Polysaccharide Antigen of Group B Streptococci Using Cyclohexane-1, 2-diacetal (CDA) Protected Rhamnosides // Angewandte Chemie International Edition in English. – 1994. – Т. 33, № 22. – C. 2292-2294. http://dx.doi.org/10.1002/anie.199422921

L. Douglas N., V. Ley S., Lucking U., L. warriner S. Tuning glycoside reactivity: New tool for efficient oligosaccharide synthesis // J. Chem. Soc., Perkin Trans. 1. – 1998. – № 1. – C. 51-66. http://dx.doi.org/10.1039/a705275h

zhang z., Ollmann I.R., Ye X.-S., wischnat R., Baasov T., wong C.-H. Programmable One-Pot Oligosaccharide Synthesis // J. Amer. Chem. Soc. – 1999. – Т. 121, № 4. – C. 734-753.

Burkhart F., zhang z., wacowich-Sgarbi S., wong C.-H. Synthesis of the Globo H Hexasaccharide Using the Programmable Reactivity-Based One-Pot Strategy // Angew. Chem. Int. Ed. Engl. – 2001. – Т. 40, № 7. – C. 1274-1277. http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1274::aid-anie1274>3.0.co;2-w

Sears P., wong C.H. Toward automated synthesis of oligosaccharides and glycoproteins // Science (New York, N.Y.). – 2001. – Т. 291, № 5512. – C. 2344-2350. http://dx.doi.org/10.1126/science.1058899

wang C.-C., Lee J.-C., Luo S.-Y., Kulkarni S.S., Huang Y.-w., Lee C.-C., Chang K.-L., Hung S.-C. Regioselective one-pot protection of carbohydrates // Nature. – 2007. – Т. 446, № 7138. – C. 896-899.

Danishefsky S.J., McClure K.F., Randolph J.T., Ruggeri R.B. A strategy for the solid-phase synthesis of oligosaccharides // Science (New York, N.Y.). – 1993. – Т. 260, № 5112. – C. 1307-1309. http://dx.doi.org/10.1126/science.8493573

Halcomb R.L., Huang H., wong C.-H. Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion // J. Amer. Chem. Soc. – 1994. – Т. 116, № 25. – C. 11315-11322.

Seeberger P.H., Haase w.C. Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries // Chem. Rev. – 2000. – Т. 100, № 12. – C. 4349-4394.

Yamada H., Imamura K., Takahashi T. Synthesis of a branched oligosaccharide by remote glycosidation // Tetrahedron Lett. – 1997. – Т. 38, № 3. – C. 391-394. http://dx.doi.org/10.1016/s0040-4039(96)02196-x

Fraser-Reid B., Udodong U.E., wu z., Ottosson H., Merritt J.R., Rao C.S., Roberts C., Madsen R. n-Pentenyl Glycosides in Organic Chemistry: A Contemporary Example of Serendipity // Synlett. – 1992. – Т. 1992, № 12. – C. 927-942. http://dx.doi.org/10.1055/s-1992-21543

Boons G.-J., Grice P., Leslie R., Ley S.V., Yeung L.L. Dispiroketals in synthesis (Part 5): A new opportunity for oligosaccharide synthesis using differentially activated glycosyl donors and acceptors // Tetrahedron Lett. – 1993. – Т. 34, № 52. – C. 8523-8526. http://dx.doi.org/10.1016/s0040-4039(00)61375-8

Koeller K.M., wong C.H. Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies // Chem. Rev. – 2000. – Т. 100, № 12. – C. 4465-4494. http://dx.doi.org/10.1021/cr990297n

wong C.-H., Ye X.-S., zhang z. Assembly of Oligosaccharide Libraries with a Designed Building Block and an Efficient Orthogonal Protection−Deprotection Strategy // J. Amer. Chem. Soc. – 1998. – Т. 120, № 28. – C. 7137-7138. http://dx.doi.org/10.1021/ja9813616

Misra A.K., Roy N. Synthesis of the Tetrasaccharide Repeating Unit of the Antigen from Escherichia coli O126 as Its Methyl Glycoside // J. Carbohydr. Chem. – 1998. – Т. 17, № 7. – C. 1047-1056. http://dx.doi.org/10.1080/07328309808001883

Yamada H., Kato T., Takahashi T. One-pot sequential glycosylation:A new method for the synthesis of branched oligosaccharides // Tetrahedron Lett. – 1999. – Т. 40, № 24. – C. 4581-4584. http://dx.doi.org/10.1016/s0040-4039(99)00796-0

Takahashi T., Adachi M., Matsuda A., Doi T. Combinatorial synthesis of trisaccharides via solution-phase one-pot glycosylation // Tetrahedron Lett. – 2000. – Т. 41, № 15. – C. 2599-2603. http://dx.doi.org/10.1016/s0040-4039(00)00214-8

Geurtsen R., Holmes D.S., Boons G.J. Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations // J. Org. Chem. – 1997. – Т. 62, № 23. – C. 8145-8154. http://dx.doi.org/10.1021/jo971233k

Holemann A., Seeberger P.H. Carbohydrate diversity: synthesis of glycoconjugates and complex carbohydrates // Curr. Opin. Biotechnol. – 2004. – Т. 15, № 6. – C. 615-622. http://dx.doi.org/10.1016/j.copbio.2004.10.001

Daines A.M., Maltman B.A., Flitsch S.L. Synthesis and modifications of carbohydrates, using biotransformations // Curr. Opin. Chem. Biol. – 2004. – Т. 8, № 2. – C. 106-113. http://dx.doi.org/10.1016/j.cbpa.2004.02.003

wu C.Y., wong C.H. Programmable one-pot glycosylation // Top. Curr. Chem. – 2011. – Т. 301, – C. 223-252. http://dx.doi.org/10.1007/128_2010_109

Grice P., Ley S.V., Pietruszka J., Osborn H.M.I., Priepke H.w.M., warriner S.L. A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane-1,2-diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide // Chem. Eur. J. – 1997. – Т. 3, № 3. – C. 431-440. http://dx.doi.org/10.1002/chem.19970030315

Garegg P.J. Thioglycosides as glycosyl donors in oligosaccharide synthesis // Adv. Carbohydr. Chem. Biochem. – 1997. – Т. 52, – C. 179-205. http://dx.doi.org/10.1016/s0065-2318(08)60091-8


Пристатейна бібліографія ГОСТ


1. Varki A. Biological roles of oligosaccharides: all of the theories are correct // Glycobiology. – 1993. – Т. 3, № 2. – C. 97-130. http://dx.doi.org/10.1093/glycob/3.2.97 


2.  Lehninger A.L.N., D.L.; Cox, M.M.  Principles of Biochemistry. 2nd Ed. — N.Y. : worth Publishers Inc., 2000.


3.  Phillips M.L., Nudelman E., Gaeta F.C., Perez M., Singhal A.K., Hakomori S., Paulson J.C. ELAM-1 mediates cell adhesion by recognition of a carbohydrate ligand, sialyl-Lex // Science (New York, N.Y.). – 1990. – Т. 250, № 4984. – C. 1130-1132. http://dx.doi.org/10.1126/science.1701274


4.  Lasky L.A. Selectins: interpreters of cell-specific carbohydrate information during inflammation // Science (New York, N.Y.). – 1992. – Т. 258, № 5084. – C. 964-969. http://dx.doi.org/10.1126/science.1439808 


5. wong C.H. Carbohydrate-based Drug Discovery. : wiley, 2006.


6.  Hurtley S., Service R., Szuromi P. Cinderella’s Coach Is Ready // Science (New York, N.Y.). – 2001. – Т. 291, № 5512. – C. 2337. http://dx.doi.org/10.1126/science.291.5512.2337 


7.  Spohr U., Lemieux R.U. Synthetic, conformational, and immunochemical studies of modified Lewis b and Y human blood-group determinants to serve as probes for the combining site of the lectin IV of Griffonia simplicifolia // Carbohydrate Res. – 1988. – Т. 174,–C.211-237. http://dx.doi.org/10.1016/0008-6215(88)85093-6 


8.  Cipolla L., Peri F., Airoldi C. Glycoconjugates in cancer therapy // Anticancer Agents Med. Chem. – 2008. – Т.  8, № 1. – C. 92-121. http://dx.doi.org/10.2174/187152008783330815 


9.  Levy D.E., Tang P.C., Musser J.H. Chapter 22. Cell Adhesion and Carbohydrates // Annual Reports in Medicinal Chemistry Т. Volume 29. James A.B. : Academic Press, 1994. — C. 215-224.


10.  Bioactive Carbohydrate Polymers. Т. Series Volume 44. / Ed.: Paulsen B.S. — Dordrecht. Boston. London. : Klumer Academic Publishers, 2000. — 157.


11.  Davis A.P., wareham R.S. Carbohydrate Recognition through Noncovalent Interactions: A Challenge for Biomimetic and Supramolecular Chemistry // Angew. Chem. Int. Ed. Engl. – 1999. – Т. 38, № 20. – C. 2978-2996. http://dx.doi.org/10.1002/(sici)1521-3773(19991018)38:20<2978::aid-anie2978>3.0.co;2-p 

12.  Mazik M. Molecular recognition of carbohydrates by acyclic receptors employing noncovalent interactions // Chem. Soc. Rev. – 2009. – Т. 38, № 4. – C. 935-956. http://dx.doi.org/10.1039/b710910p 


13.  Audette G.F., Delbaere L.T., Xiang J. Mapping protein: carbohydrate interactions // Curr. Protein Pept. Sci. –  2003. – Т. 4, № 1. – C. 11-20. http://dx.doi.org/10.2174/1389203033380322 


14.  G. Davis B. Recent developments in glycoconjugates // J. Chem. Soc., Perkin Trans. 1. – 1999. – № 22. – C.  3215-3237. http://dx.doi.org/10.1039/a809773i 


15.  Randolph J.T., Danishefsky S.J. Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: the first synthesis of a complex saponin // J. Amer. Chem. Soc. – 1993. – Т. 115, № 18. – C.  8473-8474.


16.  Danishefsky S.J., Bilodeau M.T. Glycals in Organic Synthesis: The Evolution of Comprehensive Strategies for the Assembly of Oligosaccharides and Glycoconjugates of Biological Consequence // Angew. Chem. Int. Ed. Engl. – 1996. – Т. 35, № 13-14. – C. 1380-1419. http://dx.doi.org/10.1002/anie.199613801 


17.  Hsu C.-H., Hung S.-C., wu C.-Y., wong C.-H. Toward Automated Oligosaccharide Synthesis // Angew. Chem. Int. Ed. Engl. – 2011. – Т. 50, № 50. – C. 11872-11923. http://dx.doi.org/10.1002/anie.201100125 


18.  Yamada H., Harada T., Takahashi T. Synthesis of An Elicitor-Active Hexaglucoside Analog by a One-Pot, Two-Step Glycosidation Procedure // J. Amer. Chem. Soc. – 1994. – Т. 116, № 17. – C. 7919-7920. http://dx.doi.org/10.1021/ja00096a068 


19.  Raghavan S., Kahne D. A one step synthesis of the ciclamycin trisaccharide // J. Amer. Chem. Soc. – 1993. – Т.  115, № 4. – C. 1580-1581. http://dx.doi.org/10.1021/ja00057a056 


20.  Ley S.V., Priepke H.w.M. A Facile One-Pot Synthesis of a Trisaccharide Unit from the Common Polysaccharide Antigen of Group B Streptococci Using Cyclohexane-1, 2-diacetal (CDA) Protected Rhamnosides // Angewandte Chemie International Edition in English. – 1994. – Т. 33, № 22. – C. 2292-2294. http://dx.doi.org/10.1002/anie.199422921 


21.  L. Douglas N., V. Ley S., Lucking U., L. warriner S. Tuning glycoside reactivity: New tool for efficient oligosaccharide synthesis // J. Chem. Soc., Perkin Trans. 1. – 1998. – № 1. – C. 51-66.  http://dx.doi.org/10.1039/a705275h 


22.zhang z., Ollmann I.R., Ye X.-S., wischnat R., Baasov T., wong C.-H. Programmable One-Pot Oligosaccharide Synthesis // J. Amer. Chem. Soc. – 1999. – Т. 121, № 4. – C. 734-753.


23.  Burkhart F., zhang z., wacowich-Sgarbi S., wong C.-H. Synthesis of the Globo H Hexasaccharide Using the Programmable Reactivity-Based One-Pot Strategy // Angew. Chem. Int. Ed. Engl. – 2001. – Т. 40, № 7. – C.  1274-1277. http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1274::aid-anie1274>3.0.co;2-w 


24.  Sears P., wong C.H. Toward automated synthesis of oligosaccharides and glycoproteins // Science (New York, N.Y.). – 2001. – Т. 291, № 5512. – C. 2344-2350. http://dx.doi.org/10.1126/science.1058899 


25.wang C.-C., Lee J.-C., Luo S.-Y., Kulkarni S.S., Huang Y.-w., Lee C.-C., Chang K.-L., Hung S.-C. Regioselective one-pot protection of carbohydrates // Nature. – 2007. – Т. 446, № 7138. – C. 896-899.


26.  Danishefsky S.J., McClure K.F., Randolph J.T., Ruggeri R.B. A strategy for the solid-phase synthesis of oligosaccharides // Science (New York, N.Y.). – 1993. – Т. 260, № 5112. – C. 1307-1309. http://dx.doi.org/10.1126/science.8493573 


27.  Halcomb R.L., Huang H., wong C.-H. Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment  and E-Selectin-Mediated Leukocyte Adhesion // J. Amer. Chem. Soc. – 1994. – Т. 116, № 25. – C. 11315-11322.


28.  Seeberger P.H., Haase w.C. Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries // Chem. Rev. – 2000. – Т. 100, № 12. – C. 4349-4394.


29.  Yamada H., Imamura K., Takahashi T. Synthesis of a branched oligosaccharide by remote glycosidation // Tetrahedron Lett. – 1997. – Т. 38, № 3. – C. 391-394. http://dx.doi.org/10.1016/s0040-4039(96)02196-x 


30.  Fraser-Reid B., Udodong U.E., wu z., Ottosson H., Merritt J.R., Rao C.S., Roberts C., Madsen R. n-Pentenyl Glycosides in Organic Chemistry: A Contemporary Example of Serendipity // Synlett. – 1992. – Т. 1992, № 12. – C. 927-942. http://dx.doi.org/10.1055/s-1992-21543 


31.  Boons G.-J., Grice P., Leslie R., Ley S.V., Yeung L.L. Dispiroketals in synthesis (Part 5): A new opportunity for oligosaccharide synthesis using differentially activated glycosyl donors and acceptors // Tetrahedron Lett. – 1993. – Т. 34, № 52. – C. 8523-8526.  http://dx.doi.org/10.1016/s0040-4039(00)61375-8 


32.  Koeller K.M., wong C.H. Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies // Chem. Rev. – 2000. – Т. 100, № 12. – C. 4465-4494. http://dx.doi.org/10.1021/cr990297n 


33.wong C.-H., Ye X.-S., zhang z. Assembly of Oligosaccharide Libraries with a Designed Building Block and an Efficient Orthogonal Protection−Deprotection Strategy // J. Amer. Chem. Soc. – 1998. – Т. 120, № 28. – C.  7137-7138. http://dx.doi.org/10.1021/ja9813616 


34.  Misra A.K., Roy N. Synthesis of the Tetrasaccharide Repeating Unit of the Antigen from Escherichia coli O126 as Its Methyl Glycoside // J. Carbohydr. Chem. – 1998. – Т. 17, № 7. – C. 1047-1056. http://dx.doi.org/10.1080/07328309808001883 


35.  Yamada H., Kato T., Takahashi T. One-pot sequential glycosylation:A new method for the synthesis of branched oligosaccharides // Tetrahedron Lett. – 1999. – Т. 40, № 24. – C. 4581-4584.  http://dx.doi.org/10.1016/s0040-4039(99)00796-0 


36.  Takahashi T., Adachi M., Matsuda A., Doi T. Combinatorial synthesis of trisaccharides via solution-phase one-pot glycosylation // Tetrahedron Lett. – 2000. – Т. 41, № 15. – C. 2599-2603.  http://dx.doi.org/10.1016/s0040-4039(00)00214-8 

37.  Geurtsen R., Holmes D.S., Boons G.J. Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations // J. Org. Chem. – 1997. – Т. 62, № 23. – C. 8145-8154.  http://dx.doi.org/10.1021/jo971233k 


38.  Holemann A., Seeberger P.H. Carbohydrate diversity: synthesis of glycoconjugates and complex carbohydrates // Curr. Opin. Biotechnol. – 2004. – Т. 15, № 6. – C. 615-622. http://dx.doi.org/10.1016/j.copbio.2004.10.001 


39.  Daines A.M., Maltman B.A., Flitsch S.L. Synthesis and modifications of carbohydrates, using biotransformations // Curr. Opin. Chem. Biol. – 2004. – Т. 8, № 2. – C. 106-113.  http://dx.doi.org/10.1016/j.cbpa.2004.02.003 


40.wu C.Y., wong C.H. Programmable one-pot glycosylation // Top. Curr. Chem. – 2011. – Т. 301, – C. 223-252. http://dx.doi.org/10.1007/128_2010_109 


41.  Grice P., Ley S.V., Pietruszka J., Osborn H.M.I., Priepke H.w.M.,  warriner S.L. A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane-1,2-diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide // Chem. Eur. J. – 1997. – Т. 3, № 3. – C. 431-440. http://dx.doi.org/10.1002/chem.19970030315 


42.  Garegg P.J. Thioglycosides as glycosyl donors in oligosaccharide synthesis // Adv. Carbohydr. Chem. Biochem. – 1997. – Т. 52, – C. 179-205.  http://dx.doi.org/10.1016/s0065-2318(08)60091-8 





DOI: https://doi.org/10.18524/2304-0947.2015.1(53).44553

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