基于DC-SIGN为靶点的抗HIV寡糖药物的合成与表征
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摘要
随着对HIV感染人体细胞的侵入过程的认识的加深,发现DC-SIGN不仅可以帮助HIV细胞的结合,而且,一旦结合以后,病毒可以更有效的攻击靶细胞,继而启动病毒在体内的复制和扩散。因而,DC-SIGN不仅参与HIV感染状态的建立,更重要的是它还参与了HIV的慢性感染过程。根据最新的HIV感染机制利用药物分子设计软件设计出以DC-SIGN为靶点的全新多糖类抗HIV药物分子。这类化合物不仅可以开发成AIDS病的治疗用药,而且可以开发为AIDS病预防用药。同时有望找到不产生耐药性的新药。我们的目的就是合成可以于DC-SIGN的糖识别结构有强作用的寡聚甘露糖。以期在世界上率先开发出以DC-SIGN为靶点的有自主知识产权的抗HIV的药物。而且,我们还设计了利用硫代氧糖苷键连接单糖的寡糖分子,以解决寡糖在体内容易被体内的水解酶水解的问题。
Dendritic cell specific intracellular adhesion molecule–3 (ICAM-3) grabbing nonintegrin (DC-SIGN) can bind to the HIV surface protein gp120. It has been shown to be largely responsible for the ability of dendritic cells to efficiently capture and present HIV-1 to receptor-positive cells. DC-SIGNR, a receptor that is 77% identical in sequence to DC-SIGN also can bind HIV. Crystal structure of DC-SIGN(R) with pentasaccharide complex has been solved. Based on the crystal structure of DC-SIGN/DC-SIGNR and considering the saccharide stability in physical condition, We designed a thio- trisaccharide as an anti-HIV agent for the AIDS chemotherapy and prevention. The synthesis work has been accomplished in good yield. The assay of its anti-HIV activity is in progress and will be reported in near future.
Dendritic cell specific intracellular adhesion molecule–3 (ICAM-3) grabbing nonintegrin (DC-SIGN) can bind to the HIV surface protein gp120. It has been shown to be largely responsible for the ability of dendritic cells to efficiently capture and present HIV-1 to receptor-positive cells. DC-SIGNR, a receptor that is 77% identical in sequence to DC-SIGN also can bind HIV. Crystal structure of DC-SIGN(R) with pentasaccharide complex has been solved. Based on the crystal structure of DC-SIGN/DC-SIGNR and considering the saccharide stability in physical condition, We designed a thio- trisaccharide as an anti-HIV agent for the AIDS chemotherapy and prevention. The synthesis work has been accomplished in good yield. The assay of its anti-HIV activity is in progress and will be reported in near future.
引文
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2. Louise A. Cooley, Sharon R. Lewin, HIV-1 cell entry and advances in viral entry inhibitor therapy, Journal of Clinical Virology Vol.26 2003 121-132
3. Peter D. Kwong, Michael L. Doyle, David J. Casper, Claudia C., HIV-1 evades antibody-mediated neutralization through conformation al masking of receptor-binding sites, Nature Vol.420 2002 678- 682
4. Theodore Jardetzky, Conformational camouflage, Nature, Vol.420 2002 623-624
5. Ashraf Brik, Ying-Chuan Lin, John Elder, Chi-Huey Wong, A quick diversity-oriented amide-forming reaction to optimize P-subsite residues, Chemistry and Biology, Vol.9 2002 891-896
6. Carole A. Bewley, Shigeki Kiyonaka, Itaru Hamachi, Site-specific discrimination by cyanovirin-N for α-linked trisaccharides comprising the three arms of Man8 and Man9, J. Mol. Biol. Vol.322 2002 881-889
7. Brent A. Williams, Mary C. Chervenak, Eric J. Toone, Energetics of lectin-carbohydrate binding, The Journal of Biological Chemistry Vol.267 No.32 1992 22907-22911
8. Dipak K. Mandal, C. Fred Brewer, Differences in the binding affinities of dimeric concanavalin A(including acetyl and succinyl derivatives) and tetrameric concanavalin A with large oligomannose-type glycopeptides, Biochemistry Vol.32 1993 5116-5120
9. Hongbing Liu, Wendong Yu, Li-Ying Liou, Andrew P. Rice, Isol- ation and characterization of the human DC-SIGN and DC-SIGNR
promoters, Gene Vol.33 2003 149-159
10. Gerd Bendas, Jan Vogel, Udo Bakowski, Annett Krause, Jana Mu ller, Ulrich Rothe, A liposome-based model system for the simulation of lectin-induced cell adhesion, Biochimica et Biophysica Acta Vol.1325 1997 297–308
11. Dipak K. Mandal, Lokesh Bhattacharyya, Seymour H. Koenig, C. Fred Brewer, Studies of the binding specificity of Concanavalin A. nature of the Extended binding site for Asparagine-linked carbohydrates, Biochemistry Vol.33 1994 1157-1162
12. Lucy East, Clare M. Isacke, The mannose receptor family, Biochimica et Biophysica Acta Vol.1572 2002 364-386
13. 陈海峰,陈观今,HIV-1 感染引起的细胞调亡机制及相关的病毒基因,中国人兽共患病杂志,18 2002 105-108
14.王颖,王晓峰,傅学奇,HIV-1 复制抑制剂的新靶标,生命的化学,Vol.21 2001 485-487
15.魏文青,卢洁,王明霞,抗艾滋病药物的研究进展,国外医学药学分册,Vol.28 2001 294-297
16. Hadar Feinberg, Daniel A. Mitchell, Kurt Drickamer, William I. Weis, Structural basis for selective recognition of oligosaccharides by DC-SIGN and DC-SIGNR, Science Vol. 294 2001 2163-2166
17. Stephen A. Parent, Theresa Zhang, Gary Chrebet,Joseph A. Clem- as, Molecular characterization of the murine SIGNR1 gene encoding a C-type lectin homologous to human DC-SIGN and DC-SIGNR, Gene Vol.293 2002 33–46
18. Carole A. Bewley, Shigeki Kiyonaka, Itaru Hamachi, Site-specific Discrimination by Cyanovirin-N for α-Linked Trisaccharides Compr ising the Three Arms of Man8 and Man9, J. Mol. Biol. Vol.322 2002 881–889
19. Graham Simmons, Jacqueline D. Reeves, Case C. Grogan, DC- SIGN and DC-SIGNR Bind Ebola Glycoproteins and Enhance Infec
tion of Macrophages and Endothelial Cells, Virology Vol.305 2003 115 –123
20. Elizabeth J. Soilleux, Nicholas Coleman, Transplacental transmis- sion of HIV: a potential role for HIV binding lectins,The International Journal of Biochemistry & Cell Biology Vol.35 2003 283–287
21. Stefan P?hlmann, Frédéric Baribaud and Robert W. Doms, DC- SIGN and DC-SIGNR: helping hands for HIV, TRENDS in Immun- ology Vol.22 No.12 2001 643-646
22. Diederik A. Bleijs, Teunis B.H. Geijtenbeek, Carl G. Figdor, DC- SIGN and LFA-1: a battle for ligand, TRENDS in Immunology Vol. 22 No.8 2001 457-463
23. Andrew K. Sewell, David A. Price, Dendritic cells and transmiss ion of HIV-1, TRENDS in Immunology Vol.22 No.4 2001 173-175
24. Anneke Engering, Teunis B.H. Geijtenbeek, Yvette van Kooyk, Immune escape through C-type lectinson dendritic cells, TRENDS in Immunology Vol.23 No.10 2002 480-485
25. Robert Keller, Dendritic cells: their significance in health and dise ase, Immunology Letters Vol.78 2001 113–122
26. Eric Duverger, Natacha Frison, Annie-Claude Roche, Carbohydra te-lectin interactions assessed by surface plasmon resonance, Biochim ie Vol.85 2003 167–179
27. Teunis B. H. Geijtenbeek, Gerrit Koopman, Gerard C. F. van Duij nhoven, Rhesus macaque and chimpanzee DC-SIGN act as HIV/SIV
gp120 trans-receptors, similar to human DC-SIGN, Immunology Lett ers Vol.79 2001 101–107
28. Yvette van Kooyk, Ben Appelmelk, Teunis B.H. Geijtenbeek, A fatal attraction: Mycobacterium tuberculosis and HIV-1 target DC- SIGN to escape immune surveillance, TRENDS in Molecular Medic ine Vol.9 No.4 2003 153-159
29. Stuart G. Turville, Jim Arthos, Kelli Mac Donald, Garry Lynch,
HIV gp120 receptors on human dendritic cells, BLOOD Vol. 98 2001
2482-2488
30. Stuart G. Turville, Paul U. Cameron, James Arthos, Bitter-sweet symphony: defining the role of dendritic cell gp120 receptors in HIV infection, Journal of Clinical Virology Vol.22 2001 229–239
31. Teunis B. H. Geijtenbeek, Douglas S. kwon, Ruurd Torensma, Sandra J. van Vliet etal, DC-SIGN a dendritic cell-specific HIV-1-binding protein that enhances trans-infection of T cells, Cell Vol.100 2000 587-597
32. Tomoya Ogawa, Masanao Matasui, Regioselective enhancement of the nucleophilicity of hydroxyl groups through trialkystannylation: a route to partial alkylation of polyhydroxy compounds, Carbohydrate Research Vol.62 1978 C1-C4
33. William A Bonner, Isomers of tetra-O-acetyl-D-mannopyranose, Journal of Organic Chemistry, Vol.80 1958 3372-3379
34. Kaichang Li, Richard F. Helm, A practical synthesis of methyl 4-O-methyl-α-glucopyranosiduronic acid, Carbohydrate Research Vol.273 1995 249-253
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36. Jacques Defaye, Hugues Driguez, Eric Ohleyer, Stereoselective synthesis of 1,2-trans-related 1-thioglycoses, Carbohydrate Research Vol.130 1984 317-321
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38. Wei Wang, Fanzuo Kong, Highly Regio- and Stereoselective synthesis of mannose-containing oligosaccharides with acetobromo
sugars as the donors and partially protected mannose derivatives as the acceptors via sugar orthoester, Angew. Chem. Int. Ed. 38 1999 1247-1250
39. Laixi Wang, Yuan C. Lee, The first synthesis of N,N’-diacetyl-thio chitobiose and related compounds, Carbohydrate Letters, Vol.1 1995 185-190
40. Alois F., Ingo K., A practical synthesis of β-D-mannopyranosides, Tetrahedron Letters Vol.39 1998 5721-5724
41. Didier Dubreuil, Jeannine Cleophax, Andre Loupy, Solvent-free Benzylation of polyols by phase-transfer catalysis or supported reagent methods, Carbohydrate Research Vol.252 1994 149-157
42. Enrique Parra, Hugo-Norberto Caro, Jesus Jimenez-Barbero, Synthesis and conformational studies of carrabiose and its 4’-sulphate and 2,4’-disulphate, Carbohydrate Research Vol.208 1990 83-92
43. Daniel M. Ratner, Erika R. Swanson, Peter H. Seeberger, Automated synthesis of a protected N-linked glycoprotein core Penta- saccharide, Organic Letters, Vol.5 2004
44. Yuliang Zhu, Fanzuo Kong, A facile and effective synthesis of α-(1-6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodeca- saccharides, and β-(1-6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors, Carbohydrate Research Vol.332 2001 1–21
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46. Nathalie A. Karst, Tasneem F. Islam, Robert J. Linhardt, Sulfo-protected hexosamine monosaccharides: potentially versatile building blocks for glycosaminoglycan synthesis, Organic Letters,
Vol.5 No.25 2003 4839-4842
47. Cheng-An Tai, Suvarn S. Kulkarni, Shang-Cheng Hung, Facile Cu(OTf)2-Catalyzed Preparation of Per-O-acetylated Hexopyranoses with Stoichiometric Acetic Anhydride and Sequential One-Pot Anom eric Substitution to Thioglycosides under Solvent-Free Conditions, J. Org. Chem. Vol.68 2003 8719-8722
48. David Crich, Marco de la Mora, A. U. Vinod, Influence of the 4,6 -O-Benzylidene, 4,6-O-Phenylboronate, and 4,6-O-Polystyrylboron- ate Protecting Groups on the Stereochemical Outcome of Thioglyco side-Based Glycosylations Mediated by 1-Benzenesulfinyl Piperidine/ Triflic Anhydride and N-Iodosuccinimide/Trimethylsilyl Triflate, J. Org. Chem. Vol.68 2003 8142-8148
49. Wei Zou, Edith Lacroix, Zerong Wang, Shih-Hsiung Wu, Synthesis of thio-C-glycosides from 2’-carbonylalkyl C-glycosides by a tandem β-elimination and intramolecular hetero-Michael addition, Tetrahedron Letters Vol.44 2003 4431-4433
50. Marie-Odile Contour-Galcera, Yili Ding, Carmen Ortiz-Mellet, Jacpues Defaye, Stereocontrolled synthesis of Sulfr-Linked analogues of the branched tetrasaccharide repeating-unit of the immuno- stimulant polysaccharide schizophyllan and of its β-(1-3)-branched, β-(1-6)-linked isomer, Carbohydrate Research Vol.28 1996 119-128
51. Marie-Odile Contour-Galcera, Jean-Michel Guillot, Carmen Ortiz-Mellet, Francoise Pflieger-Carrara, Jacpues Defaye, Synthesis of sulfur-linked analogues of nigerose laminarabiose laminaratriose gentiobiose gentiotriose and laminaran trisaccharide Y, Carbohydrate Research Vol.28 1996 99-118
52. Lise Munch Mikkelsen, Troels Skrydstrup, Synthesis of the C- Linked Disaccharide α-D-Man-(1-4)-D-Man Employing a SmI2- Med iated C-Glycosylation Step: En Route to Cyclic C-Oligosaccharides, J. Org. Chem. Vol.68 2003 2123-2128
53. Vincent Moreau, Jens Chr. Norrild, Hugues Driguez, Synthesis of methyl 4-thio-β-cellobioside a reinvestigation, Carbohydrate Research Vol.300 1997 271-277
54. Angela Liakatos, Milton J. Kiefel, Mark von Itzstein, Synthesis of Lactose-Based S-Linked Sialylmimetics of α(2,3)-Sialosides, Organic Letter Vol.5 2003 4365-4368
55. Lise Munch Mikkelsen, Sussie Lerche Krintel, Jesu′s Jime′nez- Barbero, Troels Skrydstrup, Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide
α-D-Man-(1-3)-[α-D-Man-(1- 6)]-D-Man and the Disaccharides
α-D-Man-(1-3)-D-Man and α-D-Man-(1- 6)-D-Man, J. Org. Chem. Vol.67 2002 6297-6308
56. Blair D. Johnston, B. Mario Pinto, Synthesis of heteroanalogues of disaccharides as potential inhibitors of the processing mannosidase Class I enzymes, Carbohydrate Research Vol.310 1998 17-25
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2. Louise A. Cooley, Sharon R. Lewin, HIV-1 cell entry and advances in viral entry inhibitor therapy, Journal of Clinical Virology Vol.26 2003 121-132
3. Peter D. Kwong, Michael L. Doyle, David J. Casper, Claudia C., HIV-1 evades antibody-mediated neutralization through conformation al masking of receptor-binding sites, Nature Vol.420 2002 678- 682
4. Theodore Jardetzky, Conformational camouflage, Nature, Vol.420 2002 623-624
5. Ashraf Brik, Ying-Chuan Lin, John Elder, Chi-Huey Wong, A quick diversity-oriented amide-forming reaction to optimize P-subsite residues, Chemistry and Biology, Vol.9 2002 891-896
6. Carole A. Bewley, Shigeki Kiyonaka, Itaru Hamachi, Site-specific discrimination by cyanovirin-N for α-linked trisaccharides comprising the three arms of Man8 and Man9, J. Mol. Biol. Vol.322 2002 881-889
7. Brent A. Williams, Mary C. Chervenak, Eric J. Toone, Energetics of lectin-carbohydrate binding, The Journal of Biological Chemistry Vol.267 No.32 1992 22907-22911
8. Dipak K. Mandal, C. Fred Brewer, Differences in the binding affinities of dimeric concanavalin A(including acetyl and succinyl derivatives) and tetrameric concanavalin A with large oligomannose-type glycopeptides, Biochemistry Vol.32 1993 5116-5120
9. Hongbing Liu, Wendong Yu, Li-Ying Liou, Andrew P. Rice, Isol- ation and characterization of the human DC-SIGN and DC-SIGNR
promoters, Gene Vol.33 2003 149-159
10. Gerd Bendas, Jan Vogel, Udo Bakowski, Annett Krause, Jana Mu ller, Ulrich Rothe, A liposome-based model system for the simulation of lectin-induced cell adhesion, Biochimica et Biophysica Acta Vol.1325 1997 297–308
11. Dipak K. Mandal, Lokesh Bhattacharyya, Seymour H. Koenig, C. Fred Brewer, Studies of the binding specificity of Concanavalin A. nature of the Extended binding site for Asparagine-linked carbohydrates, Biochemistry Vol.33 1994 1157-1162
12. Lucy East, Clare M. Isacke, The mannose receptor family, Biochimica et Biophysica Acta Vol.1572 2002 364-386
13. 陈海峰,陈观今,HIV-1 感染引起的细胞调亡机制及相关的病毒基因,中国人兽共患病杂志,18 2002 105-108
14.王颖,王晓峰,傅学奇,HIV-1 复制抑制剂的新靶标,生命的化学,Vol.21 2001 485-487
15.魏文青,卢洁,王明霞,抗艾滋病药物的研究进展,国外医学药学分册,Vol.28 2001 294-297
16. Hadar Feinberg, Daniel A. Mitchell, Kurt Drickamer, William I. Weis, Structural basis for selective recognition of oligosaccharides by DC-SIGN and DC-SIGNR, Science Vol. 294 2001 2163-2166
17. Stephen A. Parent, Theresa Zhang, Gary Chrebet,Joseph A. Clem- as, Molecular characterization of the murine SIGNR1 gene encoding a C-type lectin homologous to human DC-SIGN and DC-SIGNR, Gene Vol.293 2002 33–46
18. Carole A. Bewley, Shigeki Kiyonaka, Itaru Hamachi, Site-specific Discrimination by Cyanovirin-N for α-Linked Trisaccharides Compr ising the Three Arms of Man8 and Man9, J. Mol. Biol. Vol.322 2002 881–889
19. Graham Simmons, Jacqueline D. Reeves, Case C. Grogan, DC- SIGN and DC-SIGNR Bind Ebola Glycoproteins and Enhance Infec
tion of Macrophages and Endothelial Cells, Virology Vol.305 2003 115 –123
20. Elizabeth J. Soilleux, Nicholas Coleman, Transplacental transmis- sion of HIV: a potential role for HIV binding lectins,The International Journal of Biochemistry & Cell Biology Vol.35 2003 283–287
21. Stefan P?hlmann, Frédéric Baribaud and Robert W. Doms, DC- SIGN and DC-SIGNR: helping hands for HIV, TRENDS in Immun- ology Vol.22 No.12 2001 643-646
22. Diederik A. Bleijs, Teunis B.H. Geijtenbeek, Carl G. Figdor, DC- SIGN and LFA-1: a battle for ligand, TRENDS in Immunology Vol. 22 No.8 2001 457-463
23. Andrew K. Sewell, David A. Price, Dendritic cells and transmiss ion of HIV-1, TRENDS in Immunology Vol.22 No.4 2001 173-175
24. Anneke Engering, Teunis B.H. Geijtenbeek, Yvette van Kooyk, Immune escape through C-type lectinson dendritic cells, TRENDS in Immunology Vol.23 No.10 2002 480-485
25. Robert Keller, Dendritic cells: their significance in health and dise ase, Immunology Letters Vol.78 2001 113–122
26. Eric Duverger, Natacha Frison, Annie-Claude Roche, Carbohydra te-lectin interactions assessed by surface plasmon resonance, Biochim ie Vol.85 2003 167–179
27. Teunis B. H. Geijtenbeek, Gerrit Koopman, Gerard C. F. van Duij nhoven, Rhesus macaque and chimpanzee DC-SIGN act as HIV/SIV
gp120 trans-receptors, similar to human DC-SIGN, Immunology Lett ers Vol.79 2001 101–107
28. Yvette van Kooyk, Ben Appelmelk, Teunis B.H. Geijtenbeek, A fatal attraction: Mycobacterium tuberculosis and HIV-1 target DC- SIGN to escape immune surveillance, TRENDS in Molecular Medic ine Vol.9 No.4 2003 153-159
29. Stuart G. Turville, Jim Arthos, Kelli Mac Donald, Garry Lynch,
HIV gp120 receptors on human dendritic cells, BLOOD Vol. 98 2001
2482-2488
30. Stuart G. Turville, Paul U. Cameron, James Arthos, Bitter-sweet symphony: defining the role of dendritic cell gp120 receptors in HIV infection, Journal of Clinical Virology Vol.22 2001 229–239
31. Teunis B. H. Geijtenbeek, Douglas S. kwon, Ruurd Torensma, Sandra J. van Vliet etal, DC-SIGN a dendritic cell-specific HIV-1-binding protein that enhances trans-infection of T cells, Cell Vol.100 2000 587-597
32. Tomoya Ogawa, Masanao Matasui, Regioselective enhancement of the nucleophilicity of hydroxyl groups through trialkystannylation: a route to partial alkylation of polyhydroxy compounds, Carbohydrate Research Vol.62 1978 C1-C4
33. William A Bonner, Isomers of tetra-O-acetyl-D-mannopyranose, Journal of Organic Chemistry, Vol.80 1958 3372-3379
34. Kaichang Li, Richard F. Helm, A practical synthesis of methyl 4-O-methyl-α-glucopyranosiduronic acid, Carbohydrate Research Vol.273 1995 249-253
35. Philippe L. Durette, Tsung Y. Shen, Insulin-link and insulin-antagonistic carbohydrate derivatives the synthesis of aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides, Carbohydrate Research Vol.81 1980 261-274
36. Jacques Defaye, Hugues Driguez, Eric Ohleyer, Stereoselective synthesis of 1,2-trans-related 1-thioglycoses, Carbohydrate Research Vol.130 1984 317-321
37. Robert J. Ferrier, Richard H. Furneaux, The chemistry of some 1-mercury(??)-thio-D-glucose compounds a new synthesis of 1-thio- sugars, Carbohydrate Research Vol.57 1977 73-83
38. Wei Wang, Fanzuo Kong, Highly Regio- and Stereoselective synthesis of mannose-containing oligosaccharides with acetobromo
sugars as the donors and partially protected mannose derivatives as the acceptors via sugar orthoester, Angew. Chem. Int. Ed. 38 1999 1247-1250
39. Laixi Wang, Yuan C. Lee, The first synthesis of N,N’-diacetyl-thio chitobiose and related compounds, Carbohydrate Letters, Vol.1 1995 185-190
40. Alois F., Ingo K., A practical synthesis of β-D-mannopyranosides, Tetrahedron Letters Vol.39 1998 5721-5724
41. Didier Dubreuil, Jeannine Cleophax, Andre Loupy, Solvent-free Benzylation of polyols by phase-transfer catalysis or supported reagent methods, Carbohydrate Research Vol.252 1994 149-157
42. Enrique Parra, Hugo-Norberto Caro, Jesus Jimenez-Barbero, Synthesis and conformational studies of carrabiose and its 4’-sulphate and 2,4’-disulphate, Carbohydrate Research Vol.208 1990 83-92
43. Daniel M. Ratner, Erika R. Swanson, Peter H. Seeberger, Automated synthesis of a protected N-linked glycoprotein core Penta- saccharide, Organic Letters, Vol.5 2004
44. Yuliang Zhu, Fanzuo Kong, A facile and effective synthesis of α-(1-6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodeca- saccharides, and β-(1-6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors, Carbohydrate Research Vol.332 2001 1–21
45. Lise Munch Mikkelsen, Troels Skrydstrup, Synthesis of the C-linked Disaccharide α-D-Man(1-4)-D-Man employing a SmI2- mediate C-glycosylation step: En route to cyclic C-oligosaccharides, Journal of Organic Chemistry Vol.68 2003 2123-2128
46. Nathalie A. Karst, Tasneem F. Islam, Robert J. Linhardt, Sulfo-protected hexosamine monosaccharides: potentially versatile building blocks for glycosaminoglycan synthesis, Organic Letters,
Vol.5 No.25 2003 4839-4842
47. Cheng-An Tai, Suvarn S. Kulkarni, Shang-Cheng Hung, Facile Cu(OTf)2-Catalyzed Preparation of Per-O-acetylated Hexopyranoses with Stoichiometric Acetic Anhydride and Sequential One-Pot Anom eric Substitution to Thioglycosides under Solvent-Free Conditions, J. Org. Chem. Vol.68 2003 8719-8722
48. David Crich, Marco de la Mora, A. U. Vinod, Influence of the 4,6 -O-Benzylidene, 4,6-O-Phenylboronate, and 4,6-O-Polystyrylboron- ate Protecting Groups on the Stereochemical Outcome of Thioglyco side-Based Glycosylations Mediated by 1-Benzenesulfinyl Piperidine/ Triflic Anhydride and N-Iodosuccinimide/Trimethylsilyl Triflate, J. Org. Chem. Vol.68 2003 8142-8148
49. Wei Zou, Edith Lacroix, Zerong Wang, Shih-Hsiung Wu, Synthesis of thio-C-glycosides from 2’-carbonylalkyl C-glycosides by a tandem β-elimination and intramolecular hetero-Michael addition, Tetrahedron Letters Vol.44 2003 4431-4433
50. Marie-Odile Contour-Galcera, Yili Ding, Carmen Ortiz-Mellet, Jacpues Defaye, Stereocontrolled synthesis of Sulfr-Linked analogues of the branched tetrasaccharide repeating-unit of the immuno- stimulant polysaccharide schizophyllan and of its β-(1-3)-branched, β-(1-6)-linked isomer, Carbohydrate Research Vol.28 1996 119-128
51. Marie-Odile Contour-Galcera, Jean-Michel Guillot, Carmen Ortiz-Mellet, Francoise Pflieger-Carrara, Jacpues Defaye, Synthesis of sulfur-linked analogues of nigerose laminarabiose laminaratriose gentiobiose gentiotriose and laminaran trisaccharide Y, Carbohydrate Research Vol.28 1996 99-118
52. Lise Munch Mikkelsen, Troels Skrydstrup, Synthesis of the C- Linked Disaccharide α-D-Man-(1-4)-D-Man Employing a SmI2- Med iated C-Glycosylation Step: En Route to Cyclic C-Oligosaccharides, J. Org. Chem. Vol.68 2003 2123-2128
53. Vincent Moreau, Jens Chr. Norrild, Hugues Driguez, Synthesis of methyl 4-thio-β-cellobioside a reinvestigation, Carbohydrate Research Vol.300 1997 271-277
54. Angela Liakatos, Milton J. Kiefel, Mark von Itzstein, Synthesis of Lactose-Based S-Linked Sialylmimetics of α(2,3)-Sialosides, Organic Letter Vol.5 2003 4365-4368
55. Lise Munch Mikkelsen, Sussie Lerche Krintel, Jesu′s Jime′nez- Barbero, Troels Skrydstrup, Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide
α-D-Man-(1-3)-[α-D-Man-(1- 6)]-D-Man and the Disaccharides
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