4-C-Me-DAB and 4-C-Me-LAB—enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group
The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pKa of the salt around 8.4] is discussed and illustrate...
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| Veröffentlicht in: | Tetrahedron letters 2011-01, Vol.52 (2), p.219-223 |
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| creator | Cruz, Filipa P. da Newberry, Scott Jenkinson, Sarah F. Wormald, Mark R. Butters, Terry D. Alonzi, Dominic S. Nakagawa, Shinpei Becq, Frederic Norez, Caroline Nash, Robert J. Kato, Atsushi Fleet, George W.J. |
| description | The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pKa of the salt around 8.4] is discussed and illustrates the need for care in the analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase Ki 0.89μM, IC50 0.41μM) is a competitive—whereas 4-C-Me-LAB (for rat intestinal sucrase Ki 0.95μM, IC50 0.66μM) is a non-competitive—specific and potent α-glucosidase inhibitor. A rationale for the α-glucosidase inhibition by DAB, LAB, 4-C-Me-DAB, 4-C-Me-LAB and isoDAB—but not isoLAB—is provided. Both are inhibitors of endoplasmic reticulum (ER) resident α-glucosidase I and II. |
| doi_str_mv | 10.1016/j.tetlet.2010.10.173 |
| format | Article |
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The effect of pH on the NMR spectra of 4-C-Me-DAB [pKa of the salt around 8.4] is discussed and illustrates the need for care in the analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase Ki 0.89μM, IC50 0.41μM) is a competitive—whereas 4-C-Me-LAB (for rat intestinal sucrase Ki 0.95μM, IC50 0.66μM) is a non-competitive—specific and potent α-glucosidase inhibitor. A rationale for the α-glucosidase inhibition by DAB, LAB, 4-C-Me-DAB, 4-C-Me-LAB and isoDAB—but not isoLAB—is provided. Both are inhibitors of endoplasmic reticulum (ER) resident α-glucosidase I and II.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2010.10.173</identifier><identifier>PMID: 21157573</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>acetone ; alpha-glucosidase ; Chemical Sciences ; endoplasmic reticulum ; enzyme inhibitors ; Human health and pathology ; inhibitory concentration 50 ; Life Sciences ; nuclear magnetic resonance spectroscopy ; Organic chemistry ; Pharmaceutical sciences ; Pharmacology ; Pulmonology and respiratory tract ; rats ; sucrose alpha-glucosidase ; Tissues and Organs</subject><ispartof>Tetrahedron letters, 2011-01, Vol.52 (2), p.219-223</ispartof><rights>2010 Elsevier Ltd</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c521t-82eb4378376197dc228353e3461fd31bd489e1256bb3bc520c1f2745dca5db923</citedby><cites>FETCH-LOGICAL-c521t-82eb4378376197dc228353e3461fd31bd489e1256bb3bc520c1f2745dca5db923</cites><orcidid>0000-0003-3915-0973</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2010.10.173$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21157573$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00580432$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Cruz, Filipa P. da</creatorcontrib><creatorcontrib>Newberry, Scott</creatorcontrib><creatorcontrib>Jenkinson, Sarah F.</creatorcontrib><creatorcontrib>Wormald, Mark R.</creatorcontrib><creatorcontrib>Butters, Terry D.</creatorcontrib><creatorcontrib>Alonzi, Dominic S.</creatorcontrib><creatorcontrib>Nakagawa, Shinpei</creatorcontrib><creatorcontrib>Becq, Frederic</creatorcontrib><creatorcontrib>Norez, Caroline</creatorcontrib><creatorcontrib>Nash, Robert J.</creatorcontrib><creatorcontrib>Kato, Atsushi</creatorcontrib><creatorcontrib>Fleet, George W.J.</creatorcontrib><title>4-C-Me-DAB and 4-C-Me-LAB—enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group</title><title>Tetrahedron letters</title><addtitle>Tetrahedron Lett</addtitle><description>The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pKa of the salt around 8.4] is discussed and illustrates the need for care in the analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase Ki 0.89μM, IC50 0.41μM) is a competitive—whereas 4-C-Me-LAB (for rat intestinal sucrase Ki 0.95μM, IC50 0.66μM) is a non-competitive—specific and potent α-glucosidase inhibitor. A rationale for the α-glucosidase inhibition by DAB, LAB, 4-C-Me-DAB, 4-C-Me-LAB and isoDAB—but not isoLAB—is provided. Both are inhibitors of endoplasmic reticulum (ER) resident α-glucosidase I and II.</description><subject>acetone</subject><subject>alpha-glucosidase</subject><subject>Chemical Sciences</subject><subject>endoplasmic reticulum</subject><subject>enzyme inhibitors</subject><subject>Human health and pathology</subject><subject>inhibitory concentration 50</subject><subject>Life Sciences</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Organic chemistry</subject><subject>Pharmaceutical sciences</subject><subject>Pharmacology</subject><subject>Pulmonology and respiratory tract</subject><subject>rats</subject><subject>sucrose alpha-glucosidase</subject><subject>Tissues and Organs</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kkGO0zAUhiMEYsrADRB4CYsUO46TVEhInQ4wSEUsYNaWY78kLqkdbKdSdxxiLsGSi3AIToLblBGwwJvIL__3572XP0keEzwnmBQvNvMAoYcwz_CxNCclvZPMSFXSlLKK3E1mGOc4zTFdnCUPvN_geIoK30_OMkJYyUo6S77l6Sp9D-nl8gIJo9Dpul5e_Px6A0aYoO0WnJZI9J_3fVo7YWQHCg1752yvlTaA9FYb68dWOB8p4QD5AaRuDlT0HGwAE9CP72nbj9J6rYSPkOl0rYN1_iUSEoKNRsKj0EXa9oAGFzEZtGlR6-w4PEzuNaL38Oj0PE-u37z-tLpK1x_evlst16lkGQlplUGd07KiZUEWpZJZVlFGgeYFaRQltcqrBZCMFXVN64hgSZqszJmSgql6kdHz5NXkO4z1FpSMrTvR88HprXB7boXmf78xuuOt3XEa18toEQ2eTwbdP9jVcs0PtSircE6zHYnaZ6ePOftlBB_4VnsJfS8M2NFzEptnOS1KFqX5JJXOeu-gufUmmB8SwTd8SgQ_JOJYLWnEnvw5zi30OwJR8HQSNMJy0Trt-fXH6MCmuBwHOm0E4tp3Ghz3UoORoLSLf4grq__fwy_vHdb7</recordid><startdate>20110112</startdate><enddate>20110112</enddate><creator>Cruz, Filipa P. da</creator><creator>Newberry, Scott</creator><creator>Jenkinson, Sarah F.</creator><creator>Wormald, Mark R.</creator><creator>Butters, Terry D.</creator><creator>Alonzi, Dominic S.</creator><creator>Nakagawa, Shinpei</creator><creator>Becq, Frederic</creator><creator>Norez, Caroline</creator><creator>Nash, Robert J.</creator><creator>Kato, Atsushi</creator><creator>Fleet, George W.J.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-3915-0973</orcidid></search><sort><creationdate>20110112</creationdate><title>4-C-Me-DAB and 4-C-Me-LAB—enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group</title><author>Cruz, Filipa P. da ; Newberry, Scott ; Jenkinson, Sarah F. ; Wormald, Mark R. ; Butters, Terry D. ; Alonzi, Dominic S. ; Nakagawa, Shinpei ; Becq, Frederic ; Norez, Caroline ; Nash, Robert J. ; Kato, Atsushi ; Fleet, George W.J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c521t-82eb4378376197dc228353e3461fd31bd489e1256bb3bc520c1f2745dca5db923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>acetone</topic><topic>alpha-glucosidase</topic><topic>Chemical Sciences</topic><topic>endoplasmic reticulum</topic><topic>enzyme inhibitors</topic><topic>Human health and pathology</topic><topic>inhibitory concentration 50</topic><topic>Life Sciences</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Organic chemistry</topic><topic>Pharmaceutical sciences</topic><topic>Pharmacology</topic><topic>Pulmonology and respiratory tract</topic><topic>rats</topic><topic>sucrose alpha-glucosidase</topic><topic>Tissues and Organs</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cruz, Filipa P. da</creatorcontrib><creatorcontrib>Newberry, Scott</creatorcontrib><creatorcontrib>Jenkinson, Sarah F.</creatorcontrib><creatorcontrib>Wormald, Mark R.</creatorcontrib><creatorcontrib>Butters, Terry D.</creatorcontrib><creatorcontrib>Alonzi, Dominic S.</creatorcontrib><creatorcontrib>Nakagawa, Shinpei</creatorcontrib><creatorcontrib>Becq, Frederic</creatorcontrib><creatorcontrib>Norez, Caroline</creatorcontrib><creatorcontrib>Nash, Robert J.</creatorcontrib><creatorcontrib>Kato, Atsushi</creatorcontrib><creatorcontrib>Fleet, George W.J.</creatorcontrib><collection>AGRIS</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cruz, Filipa P. da</au><au>Newberry, Scott</au><au>Jenkinson, Sarah F.</au><au>Wormald, Mark R.</au><au>Butters, Terry D.</au><au>Alonzi, Dominic S.</au><au>Nakagawa, Shinpei</au><au>Becq, Frederic</au><au>Norez, Caroline</au><au>Nash, Robert J.</au><au>Kato, Atsushi</au><au>Fleet, George W.J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>4-C-Me-DAB and 4-C-Me-LAB—enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2011-01-12</date><risdate>2011</risdate><volume>52</volume><issue>2</issue><spage>219</spage><epage>223</epage><pages>219-223</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pKa of the salt around 8.4] is discussed and illustrates the need for care in the analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase Ki 0.89μM, IC50 0.41μM) is a competitive—whereas 4-C-Me-LAB (for rat intestinal sucrase Ki 0.95μM, IC50 0.66μM) is a non-competitive—specific and potent α-glucosidase inhibitor. A rationale for the α-glucosidase inhibition by DAB, LAB, 4-C-Me-DAB, 4-C-Me-LAB and isoDAB—but not isoLAB—is provided. Both are inhibitors of endoplasmic reticulum (ER) resident α-glucosidase I and II.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>21157573</pmid><doi>10.1016/j.tetlet.2010.10.173</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-3915-0973</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | acetone alpha-glucosidase Chemical Sciences endoplasmic reticulum enzyme inhibitors Human health and pathology inhibitory concentration 50 Life Sciences nuclear magnetic resonance spectroscopy Organic chemistry Pharmaceutical sciences Pharmacology Pulmonology and respiratory tract rats sucrose alpha-glucosidase Tissues and Organs |
| title | 4-C-Me-DAB and 4-C-Me-LAB—enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group |
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