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Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions
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| Zeitschriftentitel: | Helvetica Chimica Acta |
|---|---|
| Personen und Körperschaften: | |
| In: | Helvetica Chimica Acta, 80, 1997, 6, S. 1843-1856 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
|
| Schlagwörter: |
| author_facet |
Hofmann, Thomas Hofmann, Thomas |
|---|---|
| author |
Hofmann, Thomas |
| spellingShingle |
Hofmann, Thomas Helvetica Chimica Acta Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions Inorganic Chemistry Organic Chemistry Physical and Theoretical Chemistry Drug Discovery Biochemistry Catalysis |
| author_sort |
hofmann, thomas |
| spelling |
Hofmann, Thomas 0018-019X 1522-2675 Wiley Inorganic Chemistry Organic Chemistry Physical and Theoretical Chemistry Drug Discovery Biochemistry Catalysis http://dx.doi.org/10.1002/hlca.19970800608 <jats:title>Abstract</jats:title><jats:p>The determination of the chemical structure of a previously unknown <jats:italic>Maillard</jats:italic> reaction product with an amino acid incorporated in a four‐ring structure is reported. The red compounds <jats:bold>1a</jats:bold> and <jats:bold>1b</jats:bold>, isolated from a thermally treated aqueous solution of furan‐2‐carbaldehyde and L‐alanine, were identified as (<jats:italic>S</jats:italic>)‐4{(<jats:italic>E</jats:italic>)‐1‐formyl ‐2‐(2‐furyl)ethenyl}‐5‐(2‐furyl)‐2‐{(<jats:italic>E</jats:italic>)‐(2‐furyl)methylidene}‐2, 3‐dihydro‐α‐methyl‐3‐oxo‐1<jats:italic>H</jats:italic>‐pyrrole‐1‐acetic acid and its 2‐{(<jats:italic>Z</jats:italic>)‐(2‐furyl)methylidene}isomer, respectively, by several 1D‐ and 2D‐NMR techniques, MS, UV, and IR spectroscopy as well as by synthetic experiments. 2D‐NOESY and 2D‐ROESY experiments performed for conformation analysis indicated the existence of two atropisomers.</jats:p> Determination of the Chemical Structure of novel colored 1<i>H</i>‐pyrrol‐3(2<i>H</i>)‐one derivatives formed by <i>Maillard</i>‐type reactions Helvetica Chimica Acta |
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| title |
Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_unstemmed |
Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_full |
Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_fullStr |
Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_full_unstemmed |
Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_short |
Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_sort |
determination of the chemical structure of novel colored 1<i>h</i>‐pyrrol‐3(2<i>h</i>)‐one derivatives formed by <i>maillard</i>‐type reactions |
| topic |
Inorganic Chemistry Organic Chemistry Physical and Theoretical Chemistry Drug Discovery Biochemistry Catalysis |
| url |
http://dx.doi.org/10.1002/hlca.19970800608 |
| publishDate |
1997 |
| physical |
1843-1856 |
| description |
<jats:title>Abstract</jats:title><jats:p>The determination of the chemical structure of a previously unknown <jats:italic>Maillard</jats:italic> reaction product with an amino acid incorporated in a four‐ring structure is reported. The red compounds <jats:bold>1a</jats:bold> and <jats:bold>1b</jats:bold>, isolated from a thermally treated aqueous solution of furan‐2‐carbaldehyde and L‐alanine, were identified as (<jats:italic>S</jats:italic>)‐4{(<jats:italic>E</jats:italic>)‐1‐formyl ‐2‐(2‐furyl)ethenyl}‐5‐(2‐furyl)‐2‐{(<jats:italic>E</jats:italic>)‐(2‐furyl)methylidene}‐2, 3‐dihydro‐α‐methyl‐3‐oxo‐1<jats:italic>H</jats:italic>‐pyrrole‐1‐acetic acid and its 2‐{(<jats:italic>Z</jats:italic>)‐(2‐furyl)methylidene}isomer, respectively, by several 1D‐ and 2D‐NMR techniques, MS, UV, and IR spectroscopy as well as by synthetic experiments. 2D‐NOESY and 2D‐ROESY experiments performed for conformation analysis indicated the existence of two atropisomers.</jats:p> |
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| description | <jats:title>Abstract</jats:title><jats:p>The determination of the chemical structure of a previously unknown <jats:italic>Maillard</jats:italic> reaction product with an amino acid incorporated in a four‐ring structure is reported. The red compounds <jats:bold>1a</jats:bold> and <jats:bold>1b</jats:bold>, isolated from a thermally treated aqueous solution of furan‐2‐carbaldehyde and L‐alanine, were identified as (<jats:italic>S</jats:italic>)‐4{(<jats:italic>E</jats:italic>)‐1‐formyl ‐2‐(2‐furyl)ethenyl}‐5‐(2‐furyl)‐2‐{(<jats:italic>E</jats:italic>)‐(2‐furyl)methylidene}‐2, 3‐dihydro‐α‐methyl‐3‐oxo‐1<jats:italic>H</jats:italic>‐pyrrole‐1‐acetic acid and its 2‐{(<jats:italic>Z</jats:italic>)‐(2‐furyl)methylidene}isomer, respectively, by several 1D‐ and 2D‐NMR techniques, MS, UV, and IR spectroscopy as well as by synthetic experiments. 2D‐NOESY and 2D‐ROESY experiments performed for conformation analysis indicated the existence of two atropisomers.</jats:p> |
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| imprint_str_mv | Wiley, 1997 |
| institution | DE-D161, DE-Zi4, DE-Gla1, DE-15, DE-Pl11, DE-Rs1, DE-14, DE-105, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1 |
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| spelling | Hofmann, Thomas 0018-019X 1522-2675 Wiley Inorganic Chemistry Organic Chemistry Physical and Theoretical Chemistry Drug Discovery Biochemistry Catalysis http://dx.doi.org/10.1002/hlca.19970800608 <jats:title>Abstract</jats:title><jats:p>The determination of the chemical structure of a previously unknown <jats:italic>Maillard</jats:italic> reaction product with an amino acid incorporated in a four‐ring structure is reported. The red compounds <jats:bold>1a</jats:bold> and <jats:bold>1b</jats:bold>, isolated from a thermally treated aqueous solution of furan‐2‐carbaldehyde and L‐alanine, were identified as (<jats:italic>S</jats:italic>)‐4{(<jats:italic>E</jats:italic>)‐1‐formyl ‐2‐(2‐furyl)ethenyl}‐5‐(2‐furyl)‐2‐{(<jats:italic>E</jats:italic>)‐(2‐furyl)methylidene}‐2, 3‐dihydro‐α‐methyl‐3‐oxo‐1<jats:italic>H</jats:italic>‐pyrrole‐1‐acetic acid and its 2‐{(<jats:italic>Z</jats:italic>)‐(2‐furyl)methylidene}isomer, respectively, by several 1D‐ and 2D‐NMR techniques, MS, UV, and IR spectroscopy as well as by synthetic experiments. 2D‐NOESY and 2D‐ROESY experiments performed for conformation analysis indicated the existence of two atropisomers.</jats:p> Determination of the Chemical Structure of novel colored 1<i>H</i>‐pyrrol‐3(2<i>H</i>)‐one derivatives formed by <i>Maillard</i>‐type reactions Helvetica Chimica Acta |
| spellingShingle | Hofmann, Thomas, Helvetica Chimica Acta, Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions, Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Drug Discovery, Biochemistry, Catalysis |
| title | Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_full | Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_fullStr | Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_full_unstemmed | Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_short | Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| title_sort | determination of the chemical structure of novel colored 1<i>h</i>‐pyrrol‐3(2<i>h</i>)‐one derivatives formed by <i>maillard</i>‐type reactions |
| title_unstemmed | Determination of the Chemical Structure of novel colored 1H‐pyrrol‐3(2H)‐one derivatives formed by Maillard‐type reactions |
| topic | Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Drug Discovery, Biochemistry, Catalysis |
| url | http://dx.doi.org/10.1002/hlca.19970800608 |