Stable, isotopically substituted carbohydrates: An improved synthesis of (6- 13C)aldohexoses
1,2- O-Isopropylidene-α- d- xylo-pentodialdo-1,4-furanose ( 1) has been used as the parent aldose in the preparation of d-(6- 13C)glucose and l-6- 13C)idose via cyanohydrin reduction. The addition of K 13CN (pH 6.8, 5 min) to 1 yields d- gluco and l- ido cyanohydrins that are readily reduced with H...
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| Veröffentlicht in: | Carbohydrate research 1988-04, Vol.175 (1), p.49-58 |
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| creator | King-Morris, Melinda J. Bondo, Paul B. Mrowca, Rita A. Serianni, Anthony S. |
| description | 1,2-
O-Isopropylidene-α-
d-
xylo-pentodialdo-1,4-furanose (
1) has been used as the parent aldose in the preparation of
d-(6-
13C)glucose and
l-6-
13C)idose
via cyanohydrin reduction. The addition of K
13CN (pH 6.8, 5 min) to
1 yields
d-
gluco and
l-
ido cyanohydrins that are readily reduced with H
2 and Pd-BaSO
4, to give 1,2-
O-isopropylidene-α-
d-
gluco-hexodialdo-1,4-furanose (
2; ∼65%) and 1,2-
O-isopropylidene-β-
dl-
ido-hexodialdo-1,4-furanose (
3; 35%). Aldehydes
2 and
3 are reduced
in situ with NaBH
4, the resulting alcohols are deprotected with aqueous acid, and the aldoses are chromatographed on Dowex 50 X-8 (Ca
2+) ion-exchange resin (200–400 mesh), to yield
d-(6-
13C)glucose (
6) and
l-(6-
13C)idose (
7). Molybdate epimerization of
6 and
7 yields
d-(6-
13C)mannose and
l-(6-
13C)gulose, respectively. A similar reaction scheme may be applied to methyl 2,3-
O-isopropylidene-β-
d-
ribo-pentodialdo-1,4-furanoside to generate the remaining four (6-
13C)-aldohexoses. This route is considerably simpler than the traditional Kiliani-Fischer route, and higher yields are obtained. |
| doi_str_mv | 10.1016/0008-6215(88)80155-1 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_78261778</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>0008621588801551</els_id><sourcerecordid>78261778</sourcerecordid><originalsourceid>FETCH-LOGICAL-c386t-250c0e8608c1b00d96bb9e2f3a26fd463446d0539dcac967f9e6223a4a5a95d73</originalsourceid><addsrcrecordid>eNp9kFFLHDEQx4NU9Gr9Bi3sQxGFbptsNtmsDwU5ahUEH7TggxCyySwX2ducmaz0vn1zveMefRqG_2-GmR8hnxn9ziiTPyilqpQVE-dKXSjKhCjZAZkx1fCyruTTBzLbI8fkI-JLbqls5BE54rxRVc1m5PkhmW6Ab4XHkMLKWzMM6wKnDpNPUwJXWBO7sFi7aBLgZXE1Fn65iuEtR7ge0wLQYxH64lyWBePzCzO4sIC_AQE_kcPeDAinu3pC_lz_epzflHf3v2_nV3el5UqmshLUUlCSKss6Sl0ru66Fquemkr2rJa9r6ajgrbPGtrLpW5BVxU1thGmFa_gJOdvuzXe9ToBJLz1aGAYzQphQ518laxqVwXoL2hgQI_R6Ff3SxLVmVG-k6o0xvTGmldL_pWqWx77s9k_dEtx-aGcx5193ucEssI9mtB73WCNaIVmbsZ9bDLKLNw9Ro_UwWnA-gk3aBf_-Hf8AnriSjA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>78261778</pqid></control><display><type>article</type><title>Stable, isotopically substituted carbohydrates: An improved synthesis of (6- 13C)aldohexoses</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals Complete</source><creator>King-Morris, Melinda J. ; Bondo, Paul B. ; Mrowca, Rita A. ; Serianni, Anthony S.</creator><creatorcontrib>King-Morris, Melinda J. ; Bondo, Paul B. ; Mrowca, Rita A. ; Serianni, Anthony S.</creatorcontrib><description>1,2-
O-Isopropylidene-α-
d-
xylo-pentodialdo-1,4-furanose (
1) has been used as the parent aldose in the preparation of
d-(6-
13C)glucose and
l-6-
13C)idose
via cyanohydrin reduction. The addition of K
13CN (pH 6.8, 5 min) to
1 yields
d-
gluco and
l-
ido cyanohydrins that are readily reduced with H
2 and Pd-BaSO
4, to give 1,2-
O-isopropylidene-α-
d-
gluco-hexodialdo-1,4-furanose (
2; ∼65%) and 1,2-
O-isopropylidene-β-
dl-
ido-hexodialdo-1,4-furanose (
3; 35%). Aldehydes
2 and
3 are reduced
in situ with NaBH
4, the resulting alcohols are deprotected with aqueous acid, and the aldoses are chromatographed on Dowex 50 X-8 (Ca
2+) ion-exchange resin (200–400 mesh), to yield
d-(6-
13C)glucose (
6) and
l-(6-
13C)idose (
7). Molybdate epimerization of
6 and
7 yields
d-(6-
13C)mannose and
l-(6-
13C)gulose, respectively. A similar reaction scheme may be applied to methyl 2,3-
O-isopropylidene-β-
d-
ribo-pentodialdo-1,4-furanoside to generate the remaining four (6-
13C)-aldohexoses. This route is considerably simpler than the traditional Kiliani-Fischer route, and higher yields are obtained.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/0008-6215(88)80155-1</identifier><identifier>PMID: 3378241</identifier><identifier>CODEN: CRBRAT</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Carbon Isotopes ; Chemistry ; Exact sciences and technology ; Hexoses - chemical synthesis ; Indicators and Reagents ; Isotope Labeling - methods ; Magnetic Resonance Spectroscopy ; Organic chemistry ; Preparations and properties</subject><ispartof>Carbohydrate research, 1988-04, Vol.175 (1), p.49-58</ispartof><rights>1988</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c386t-250c0e8608c1b00d96bb9e2f3a26fd463446d0539dcac967f9e6223a4a5a95d73</citedby><cites>FETCH-LOGICAL-c386t-250c0e8608c1b00d96bb9e2f3a26fd463446d0539dcac967f9e6223a4a5a95d73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0008-6215(88)80155-1$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7595619$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3378241$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>King-Morris, Melinda J.</creatorcontrib><creatorcontrib>Bondo, Paul B.</creatorcontrib><creatorcontrib>Mrowca, Rita A.</creatorcontrib><creatorcontrib>Serianni, Anthony S.</creatorcontrib><title>Stable, isotopically substituted carbohydrates: An improved synthesis of (6- 13C)aldohexoses</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>1,2-
O-Isopropylidene-α-
d-
xylo-pentodialdo-1,4-furanose (
1) has been used as the parent aldose in the preparation of
d-(6-
13C)glucose and
l-6-
13C)idose
via cyanohydrin reduction. The addition of K
13CN (pH 6.8, 5 min) to
1 yields
d-
gluco and
l-
ido cyanohydrins that are readily reduced with H
2 and Pd-BaSO
4, to give 1,2-
O-isopropylidene-α-
d-
gluco-hexodialdo-1,4-furanose (
2; ∼65%) and 1,2-
O-isopropylidene-β-
dl-
ido-hexodialdo-1,4-furanose (
3; 35%). Aldehydes
2 and
3 are reduced
in situ with NaBH
4, the resulting alcohols are deprotected with aqueous acid, and the aldoses are chromatographed on Dowex 50 X-8 (Ca
2+) ion-exchange resin (200–400 mesh), to yield
d-(6-
13C)glucose (
6) and
l-(6-
13C)idose (
7). Molybdate epimerization of
6 and
7 yields
d-(6-
13C)mannose and
l-(6-
13C)gulose, respectively. A similar reaction scheme may be applied to methyl 2,3-
O-isopropylidene-β-
d-
ribo-pentodialdo-1,4-furanoside to generate the remaining four (6-
13C)-aldohexoses. This route is considerably simpler than the traditional Kiliani-Fischer route, and higher yields are obtained.</description><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Carbon Isotopes</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Hexoses - chemical synthesis</subject><subject>Indicators and Reagents</subject><subject>Isotope Labeling - methods</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kFFLHDEQx4NU9Gr9Bi3sQxGFbptsNtmsDwU5ahUEH7TggxCyySwX2ducmaz0vn1zveMefRqG_2-GmR8hnxn9ziiTPyilqpQVE-dKXSjKhCjZAZkx1fCyruTTBzLbI8fkI-JLbqls5BE54rxRVc1m5PkhmW6Ab4XHkMLKWzMM6wKnDpNPUwJXWBO7sFi7aBLgZXE1Fn65iuEtR7ge0wLQYxH64lyWBePzCzO4sIC_AQE_kcPeDAinu3pC_lz_epzflHf3v2_nV3el5UqmshLUUlCSKss6Sl0ru66Fquemkr2rJa9r6ajgrbPGtrLpW5BVxU1thGmFa_gJOdvuzXe9ToBJLz1aGAYzQphQ518laxqVwXoL2hgQI_R6Ff3SxLVmVG-k6o0xvTGmldL_pWqWx77s9k_dEtx-aGcx5193ucEssI9mtB73WCNaIVmbsZ9bDLKLNw9Ro_UwWnA-gk3aBf_-Hf8AnriSjA</recordid><startdate>19880401</startdate><enddate>19880401</enddate><creator>King-Morris, Melinda J.</creator><creator>Bondo, Paul B.</creator><creator>Mrowca, Rita A.</creator><creator>Serianni, Anthony S.</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19880401</creationdate><title>Stable, isotopically substituted carbohydrates: An improved synthesis of (6- 13C)aldohexoses</title><author>King-Morris, Melinda J. ; Bondo, Paul B. ; Mrowca, Rita A. ; Serianni, Anthony S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-250c0e8608c1b00d96bb9e2f3a26fd463446d0539dcac967f9e6223a4a5a95d73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Carbon Isotopes</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Hexoses - chemical synthesis</topic><topic>Indicators and Reagents</topic><topic>Isotope Labeling - methods</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>King-Morris, Melinda J.</creatorcontrib><creatorcontrib>Bondo, Paul B.</creatorcontrib><creatorcontrib>Mrowca, Rita A.</creatorcontrib><creatorcontrib>Serianni, Anthony S.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>King-Morris, Melinda J.</au><au>Bondo, Paul B.</au><au>Mrowca, Rita A.</au><au>Serianni, Anthony S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stable, isotopically substituted carbohydrates: An improved synthesis of (6- 13C)aldohexoses</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1988-04-01</date><risdate>1988</risdate><volume>175</volume><issue>1</issue><spage>49</spage><epage>58</epage><pages>49-58</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>1,2-
O-Isopropylidene-α-
d-
xylo-pentodialdo-1,4-furanose (
1) has been used as the parent aldose in the preparation of
d-(6-
13C)glucose and
l-6-
13C)idose
via cyanohydrin reduction. The addition of K
13CN (pH 6.8, 5 min) to
1 yields
d-
gluco and
l-
ido cyanohydrins that are readily reduced with H
2 and Pd-BaSO
4, to give 1,2-
O-isopropylidene-α-
d-
gluco-hexodialdo-1,4-furanose (
2; ∼65%) and 1,2-
O-isopropylidene-β-
dl-
ido-hexodialdo-1,4-furanose (
3; 35%). Aldehydes
2 and
3 are reduced
in situ with NaBH
4, the resulting alcohols are deprotected with aqueous acid, and the aldoses are chromatographed on Dowex 50 X-8 (Ca
2+) ion-exchange resin (200–400 mesh), to yield
d-(6-
13C)glucose (
6) and
l-(6-
13C)idose (
7). Molybdate epimerization of
6 and
7 yields
d-(6-
13C)mannose and
l-(6-
13C)gulose, respectively. A similar reaction scheme may be applied to methyl 2,3-
O-isopropylidene-β-
d-
ribo-pentodialdo-1,4-furanoside to generate the remaining four (6-
13C)-aldohexoses. This route is considerably simpler than the traditional Kiliani-Fischer route, and higher yields are obtained.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>3378241</pmid><doi>10.1016/0008-6215(88)80155-1</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 1988-04, Vol.175 (1), p.49-58 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_78261778 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Carbon Isotopes Chemistry Exact sciences and technology Hexoses - chemical synthesis Indicators and Reagents Isotope Labeling - methods Magnetic Resonance Spectroscopy Organic chemistry Preparations and properties |
| title | Stable, isotopically substituted carbohydrates: An improved synthesis of (6- 13C)aldohexoses |
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