Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone
The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjuste...
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| Veröffentlicht in: | Journal of organic chemistry 2012-09, Vol.77 (18), p.7777-7792 |
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| container_issue | 18 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Ayers, Benjamin J Ngo, Nigel Jenkinson, Sarah F Martínez, R. Fernando Shimada, Yousuke Adachi, Isao Weymouth-Wilson, Alexander C Kato, Atsushi Fleet, George W. J |
| description | The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase inhibition of a panel of 13 glycosidases showed that 8 of the 10 stereoisomers showed significant inhibition of at least one glycosidase. |
| doi_str_mv | 10.1021/jo301243s |
| format | Article |
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Fernando ; Shimada, Yousuke ; Adachi, Isao ; Weymouth-Wilson, Alexander C ; Kato, Atsushi ; Fleet, George W. J</creator><creatorcontrib>Ayers, Benjamin J ; Ngo, Nigel ; Jenkinson, Sarah F ; Martínez, R. Fernando ; Shimada, Yousuke ; Adachi, Isao ; Weymouth-Wilson, Alexander C ; Kato, Atsushi ; Fleet, George W. J</creatorcontrib><description>The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase inhibition of a panel of 13 glycosidases showed that 8 of the 10 stereoisomers showed significant inhibition of at least one glycosidase.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo301243s</identifier><identifier>PMID: 22928735</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; Exact sciences and technology ; Glucuronates - chemistry ; Glycoside Hydrolases - antagonists & inhibitors ; Glycoside Hydrolases - chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Imino Sugars - chemical synthesis ; Imino Sugars - pharmacology ; Organic chemistry ; Preparations and properties ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Journal of organic chemistry, 2012-09, Vol.77 (18), p.7777-7792</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-3c0dd917bba045864bab173525facdfbf9398206f5cd5b7dec8dd3d5906994793</citedby><cites>FETCH-LOGICAL-a411t-3c0dd917bba045864bab173525facdfbf9398206f5cd5b7dec8dd3d5906994793</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo301243s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo301243s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26400248$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22928735$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ayers, Benjamin J</creatorcontrib><creatorcontrib>Ngo, Nigel</creatorcontrib><creatorcontrib>Jenkinson, Sarah F</creatorcontrib><creatorcontrib>Martínez, R. 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Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Glucuronates - chemistry</subject><subject>Glycoside Hydrolases - antagonists & inhibitors</subject><subject>Glycoside Hydrolases - chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Imino Sugars - chemical synthesis</subject><subject>Imino Sugars - pharmacology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0U1LHDEYB_BQLHXVHvoFJBehQqfmZTIzOYrVrSC00PY85JWNZJI1zwy4p371Rlz10lySwy__8PyD0CdKvlLC6MV95oSylsM7tKKCkaaTpD1AK0IYazjr-CE6ArgndQkhPqBDxiQbei5W6O867kyGYBU4fJs2QYc55IT1Dl_GiCnBv2ZXXA6QJ1eCweyLaL4F6_Ljrnk6hymkvHGPYc4R8M_itqo4i33JE543Dl8nlWpivQw4e7yOi1lKTjkqM-fkTtB7ryK4j_v9GP25uf599b25-7G-vbq8a1RL6dxwQ6yVtNdakVYMXauVpnUAJrwy1msvuRwY6bwwVujeOjNYy62QpJOy7SU_Rp-fc7clPywO5nEKYFyMKrm8wEgrZKTvO17p-TM1JQMU58dtCZMqu4rGp77H176rPd3HLnpy9lW-FFzB2R4oMCr6opIJ8Oa6tn5SO7w5ZaDmLyXVNv7z4D-PZ5Sg</recordid><startdate>20120921</startdate><enddate>20120921</enddate><creator>Ayers, Benjamin J</creator><creator>Ngo, Nigel</creator><creator>Jenkinson, Sarah F</creator><creator>Martínez, R. 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J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-09-21</date><risdate>2012</risdate><volume>77</volume><issue>18</issue><spage>7777</spage><epage>7792</epage><pages>7777-7792</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase inhibition of a panel of 13 glycosidases showed that 8 of the 10 stereoisomers showed significant inhibition of at least one glycosidase.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22928735</pmid><doi>10.1021/jo301243s</doi><tpages>16</tpages></addata></record> |
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| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Exact sciences and technology Glucuronates - chemistry Glycoside Hydrolases - antagonists & inhibitors Glycoside Hydrolases - chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Imino Sugars - chemical synthesis Imino Sugars - pharmacology Organic chemistry Preparations and properties Stereoisomerism Structure-Activity Relationship |
| title | Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone |
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