Proton-acceptor properties and capability for mutarotation of some glucosylamines in methanol
Graphic N-( m-Nitrophenyl)-β- d-glucopyranosylamine (Gln), N-( N-methylphenyl)-β- d-glucopyranosylamine (Glm), N-β- d-glucopyranosylpyrazole (Glp), and N-β- d-glucopyranosylimidazole (Gli) have been synthesized. Their basicity constants, p K b, determined in methanol were, respectively, 14.99, 14.36...
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| Veröffentlicht in: | Carbohydrate research 2004-06, Vol.339 (8), p.1439-1445 |
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| container_title | Carbohydrate research |
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| creator | Smiataczowa, Kazimiera Kosmalski, Jarosław Nowacki, Andrzej Czaja, Małgorzata Warnke, Zygmunt |
| description | Graphic
N-(
m-Nitrophenyl)-β-
d-glucopyranosylamine (Gln),
N-(
N-methylphenyl)-β-
d-glucopyranosylamine (Glm),
N-β-
d-glucopyranosylpyrazole (Glp), and
N-β-
d-glucopyranosylimidazole (Gli) have been synthesized. Their basicity constants, p
K
b, determined in methanol were, respectively, 14.99, 14.36, 15.04, and 9.74. The derivatives of secondary amines (Glm, Glp, and Gli) did not mutarotate in methanol in the presence of 3,5-dinitrobenzoic acid and hydrochloric acid. The heats of formation and entropies were calculated by the AM1 and PM3 methods for the glucosylamines and their cations under consideration of two plausible protonation centers. Thermodynamic parameters for the proton transfer in the reaction: glucosylamine
+
CH
3OH
2
+=glucosylamineH
+
+
CH
3OH were determined and the protonation center in the glucosylamine molecule was identified. The mechanism of mutarotation of the glucosylamines is discussed and the conclusion made that formation of an acyclic immonium cation is not a satisfactory condition for the reaction to proceed. |
| doi_str_mv | 10.1016/j.carres.2004.02.028 |
| format | Article |
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N-(
m-Nitrophenyl)-β-
d-glucopyranosylamine (Gln),
N-(
N-methylphenyl)-β-
d-glucopyranosylamine (Glm),
N-β-
d-glucopyranosylpyrazole (Glp), and
N-β-
d-glucopyranosylimidazole (Gli) have been synthesized. Their basicity constants, p
K
b, determined in methanol were, respectively, 14.99, 14.36, 15.04, and 9.74. The derivatives of secondary amines (Glm, Glp, and Gli) did not mutarotate in methanol in the presence of 3,5-dinitrobenzoic acid and hydrochloric acid. The heats of formation and entropies were calculated by the AM1 and PM3 methods for the glucosylamines and their cations under consideration of two plausible protonation centers. Thermodynamic parameters for the proton transfer in the reaction: glucosylamine
+
CH
3OH
2
+=glucosylamineH
+
+
CH
3OH were determined and the protonation center in the glucosylamine molecule was identified. The mechanism of mutarotation of the glucosylamines is discussed and the conclusion made that formation of an acyclic immonium cation is not a satisfactory condition for the reaction to proceed.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2004.02.028</identifier><identifier>PMID: 15178385</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Basicity constants ; Carbohydrate Conformation ; Glucosamine - analogs & derivatives ; Glucosamine - chemical synthesis ; Glucosamine - chemistry ; Glucosylamines ; Methanol - chemistry ; Molecular Structure ; Mutarotation ; Protons ; Thermodynamic parameters</subject><ispartof>Carbohydrate research, 2004-06, Vol.339 (8), p.1439-1445</ispartof><rights>2004 Elsevier Ltd</rights><rights>Copyright 2004 Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c424t-77b1645116fe284506fc00a306e3edc230cf27584b0012d529ed81880f35600e3</citedby><cites>FETCH-LOGICAL-c424t-77b1645116fe284506fc00a306e3edc230cf27584b0012d529ed81880f35600e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0008621504001089$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15178385$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Smiataczowa, Kazimiera</creatorcontrib><creatorcontrib>Kosmalski, Jarosław</creatorcontrib><creatorcontrib>Nowacki, Andrzej</creatorcontrib><creatorcontrib>Czaja, Małgorzata</creatorcontrib><creatorcontrib>Warnke, Zygmunt</creatorcontrib><title>Proton-acceptor properties and capability for mutarotation of some glucosylamines in methanol</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Graphic
N-(
m-Nitrophenyl)-β-
d-glucopyranosylamine (Gln),
N-(
N-methylphenyl)-β-
d-glucopyranosylamine (Glm),
N-β-
d-glucopyranosylpyrazole (Glp), and
N-β-
d-glucopyranosylimidazole (Gli) have been synthesized. Their basicity constants, p
K
b, determined in methanol were, respectively, 14.99, 14.36, 15.04, and 9.74. The derivatives of secondary amines (Glm, Glp, and Gli) did not mutarotate in methanol in the presence of 3,5-dinitrobenzoic acid and hydrochloric acid. The heats of formation and entropies were calculated by the AM1 and PM3 methods for the glucosylamines and their cations under consideration of two plausible protonation centers. Thermodynamic parameters for the proton transfer in the reaction: glucosylamine
+
CH
3OH
2
+=glucosylamineH
+
+
CH
3OH were determined and the protonation center in the glucosylamine molecule was identified. The mechanism of mutarotation of the glucosylamines is discussed and the conclusion made that formation of an acyclic immonium cation is not a satisfactory condition for the reaction to proceed.</description><subject>Basicity constants</subject><subject>Carbohydrate Conformation</subject><subject>Glucosamine - analogs & derivatives</subject><subject>Glucosamine - chemical synthesis</subject><subject>Glucosamine - chemistry</subject><subject>Glucosylamines</subject><subject>Methanol - chemistry</subject><subject>Molecular Structure</subject><subject>Mutarotation</subject><subject>Protons</subject><subject>Thermodynamic parameters</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UE1LxDAQDaK46-o_EOnJW9dJ2qbZiyDiFyzoQcGLhDSdapa2qUkq7L83Sxe8CQ-GYd57M_MIOaewpED51WaplXPolwwgXwKLEAdkTkWZpTnj74dkDgAi5YwWM3Li_Sa2wEt-TGa0oKXIRDEnHy_OBtunSmscgnXJ4OyALhj0ierrRKtBVaY1YZs0cdqNQUWBCsb2iW0SbztMPttRW79tVWf6KDN90mH4Ur1tT8lRo1qPZ_u6IG_3d6-3j-n6-eHp9mad6pzlIS3LivK8oJQ3yEReAG80gMqAY4a1ZhnohpWFyCsAyuqCrbAWVAhosoIDYLYgl5NvvP57RB9kZ7zGtlU92tHLkq6EyEoaiflE1M5677CRgzOdcltJQe5ilRs5xSp3sUpgESLKLvb-Y9Vh_Sfa5xgJ1xMB45c_Bp302mCvsTYOdZC1Nf9v-AUpD4vJ</recordid><startdate>20040601</startdate><enddate>20040601</enddate><creator>Smiataczowa, Kazimiera</creator><creator>Kosmalski, Jarosław</creator><creator>Nowacki, Andrzej</creator><creator>Czaja, Małgorzata</creator><creator>Warnke, Zygmunt</creator><general>Elsevier Ltd</general><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>20040601</creationdate><title>Proton-acceptor properties and capability for mutarotation of some glucosylamines in methanol</title><author>Smiataczowa, Kazimiera ; Kosmalski, Jarosław ; Nowacki, Andrzej ; Czaja, Małgorzata ; Warnke, Zygmunt</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c424t-77b1645116fe284506fc00a306e3edc230cf27584b0012d529ed81880f35600e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Basicity constants</topic><topic>Carbohydrate Conformation</topic><topic>Glucosamine - analogs & derivatives</topic><topic>Glucosamine - chemical synthesis</topic><topic>Glucosamine - chemistry</topic><topic>Glucosylamines</topic><topic>Methanol - chemistry</topic><topic>Molecular Structure</topic><topic>Mutarotation</topic><topic>Protons</topic><topic>Thermodynamic parameters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Smiataczowa, Kazimiera</creatorcontrib><creatorcontrib>Kosmalski, Jarosław</creatorcontrib><creatorcontrib>Nowacki, Andrzej</creatorcontrib><creatorcontrib>Czaja, Małgorzata</creatorcontrib><creatorcontrib>Warnke, Zygmunt</creatorcontrib><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>Smiataczowa, Kazimiera</au><au>Kosmalski, Jarosław</au><au>Nowacki, Andrzej</au><au>Czaja, Małgorzata</au><au>Warnke, Zygmunt</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Proton-acceptor properties and capability for mutarotation of some glucosylamines in methanol</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2004-06-01</date><risdate>2004</risdate><volume>339</volume><issue>8</issue><spage>1439</spage><epage>1445</epage><pages>1439-1445</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Graphic
N-(
m-Nitrophenyl)-β-
d-glucopyranosylamine (Gln),
N-(
N-methylphenyl)-β-
d-glucopyranosylamine (Glm),
N-β-
d-glucopyranosylpyrazole (Glp), and
N-β-
d-glucopyranosylimidazole (Gli) have been synthesized. Their basicity constants, p
K
b, determined in methanol were, respectively, 14.99, 14.36, 15.04, and 9.74. The derivatives of secondary amines (Glm, Glp, and Gli) did not mutarotate in methanol in the presence of 3,5-dinitrobenzoic acid and hydrochloric acid. The heats of formation and entropies were calculated by the AM1 and PM3 methods for the glucosylamines and their cations under consideration of two plausible protonation centers. Thermodynamic parameters for the proton transfer in the reaction: glucosylamine
+
CH
3OH
2
+=glucosylamineH
+
+
CH
3OH were determined and the protonation center in the glucosylamine molecule was identified. The mechanism of mutarotation of the glucosylamines is discussed and the conclusion made that formation of an acyclic immonium cation is not a satisfactory condition for the reaction to proceed.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>15178385</pmid><doi>10.1016/j.carres.2004.02.028</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Basicity constants Carbohydrate Conformation Glucosamine - analogs & derivatives Glucosamine - chemical synthesis Glucosamine - chemistry Glucosylamines Methanol - chemistry Molecular Structure Mutarotation Protons Thermodynamic parameters |
| title | Proton-acceptor properties and capability for mutarotation of some glucosylamines in methanol |
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