Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition
This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis...
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| Veröffentlicht in: | Journal of the American Chemical Society 1996-07, Vol.118 (29), p.6826-6840 |
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| container_end_page | 6840 |
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| container_issue | 29 |
| container_start_page | 6826 |
| container_title | Journal of the American Chemical Society |
| container_volume | 118 |
| creator | Lin, Chun-Cheng Shimazaki, Makoto Heck, Marie-Pierre Aoki, Shin Wang, Ruo Kimura, Teiji Ritzèn, Helena Takayama, Shuichi Wu, Shih-Hsiung Weitz-Schmidt, Gabriel Wong, Chi-Huey |
| description | This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Lex), Lewis Y (Ley), glycopeptides, and sialyl Lewis X (SLex) mimetics. Both α-O-fucosyl-l-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLex mimetics, and some fucopeptides prepared were 5−10 times more active than SLex as inhibitors of E-selectin. |
| doi_str_mv | 10.1021/ja952265x |
| format | Article |
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Am. Chem. Soc</addtitle><description>This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Lex), Lewis Y (Ley), glycopeptides, and sialyl Lewis X (SLex) mimetics. Both α-O-fucosyl-l-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLex mimetics, and some fucopeptides prepared were 5−10 times more active than SLex as inhibitors of E-selectin.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNptkMtOwzAQRS0EEuWx4A-8YcEiYDtx4iwRKi1SEY-AxM6a-EFcQoxiF8g_8NGkFLFiNbqac-9oLkJHlJxSwujZEkrOWM4_t9CEckYSTlm-jSaEEJYUIk930V4Iy1FmTNAJ-qqGLjYmuIC9xZWDdmjxwnyM-glfu1cTnQoYOo3vTQvRaFzFfqXiqjcBPwbXPePRjmftoHwYrbeND2-NiwZfm9h47Vv_PPz4p-_QriA6360vTZPKtEZF1-GrrnG1Wy8O0I6FNpjD37mPHi-nDxfzZHEzu7o4XySQ5jQmAKVQPM1EkVvGdQ2FhbIUKWEs1bxMOVG11VaDyJgpay2A2kIIpQtba2V5uo9ONrmq9yH0xsq33r1CP0hK5LpG-VfjyCYb1oVoPv9A6F9kXqQFlw-3lZxX2R17yubybuSPNzyoIJd-1XfjJ__kfgOCS4QC</recordid><startdate>19960724</startdate><enddate>19960724</enddate><creator>Lin, Chun-Cheng</creator><creator>Shimazaki, Makoto</creator><creator>Heck, Marie-Pierre</creator><creator>Aoki, Shin</creator><creator>Wang, Ruo</creator><creator>Kimura, Teiji</creator><creator>Ritzèn, Helena</creator><creator>Takayama, Shuichi</creator><creator>Wu, Shih-Hsiung</creator><creator>Weitz-Schmidt, Gabriel</creator><creator>Wong, Chi-Huey</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19960724</creationdate><title>Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition</title><author>Lin, Chun-Cheng ; Shimazaki, Makoto ; Heck, Marie-Pierre ; Aoki, Shin ; Wang, Ruo ; Kimura, Teiji ; Ritzèn, Helena ; Takayama, Shuichi ; Wu, Shih-Hsiung ; Weitz-Schmidt, Gabriel ; Wong, Chi-Huey</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a361t-aa98c534876f25dba7fa99830223d59350cbfdfda842e9bd8a1f788cd7fbdcf53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lin, Chun-Cheng</creatorcontrib><creatorcontrib>Shimazaki, Makoto</creatorcontrib><creatorcontrib>Heck, Marie-Pierre</creatorcontrib><creatorcontrib>Aoki, Shin</creatorcontrib><creatorcontrib>Wang, Ruo</creatorcontrib><creatorcontrib>Kimura, Teiji</creatorcontrib><creatorcontrib>Ritzèn, Helena</creatorcontrib><creatorcontrib>Takayama, Shuichi</creatorcontrib><creatorcontrib>Wu, Shih-Hsiung</creatorcontrib><creatorcontrib>Weitz-Schmidt, Gabriel</creatorcontrib><creatorcontrib>Wong, Chi-Huey</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lin, Chun-Cheng</au><au>Shimazaki, Makoto</au><au>Heck, Marie-Pierre</au><au>Aoki, Shin</au><au>Wang, Ruo</au><au>Kimura, Teiji</au><au>Ritzèn, Helena</au><au>Takayama, Shuichi</au><au>Wu, Shih-Hsiung</au><au>Weitz-Schmidt, Gabriel</au><au>Wong, Chi-Huey</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>1996-07-24</date><risdate>1996</risdate><volume>118</volume><issue>29</issue><spage>6826</spage><epage>6840</epage><pages>6826-6840</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Lex), Lewis Y (Ley), glycopeptides, and sialyl Lewis X (SLex) mimetics. Both α-O-fucosyl-l-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLex mimetics, and some fucopeptides prepared were 5−10 times more active than SLex as inhibitors of E-selectin.</abstract><pub>American Chemical Society</pub><doi>10.1021/ja952265x</doi><tpages>15</tpages></addata></record> |
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| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 1996-07, Vol.118 (29), p.6826-6840 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_ja952265x |
| source | ACS Publications |
| title | Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition |
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