Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame
The potential for dynamic chirality of an azapeptide nitrogen was examined by substitution of nitrogen for the α-carbon of the aspartate residue in the sweetener S,S-aspartame. Considering that S,S- and R,S-aspartame possess sweet and bitter tastes, respectively, a bitter-sweet taste of aza-aspart...
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| Format: | Article |
| Language: | English |
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MDPI AG
2013-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/18/12/14739 |
| _version_ | 1819089830683869184 |
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| author | Samir H. Bouayad-Gervais William D. Lubell |
| author_facet | Samir H. Bouayad-Gervais William D. Lubell |
| author_sort | Samir H. Bouayad-Gervais |
| collection | DOAJ |
| description | The potential for dynamic chirality of an azapeptide nitrogen was examined by substitution of nitrogen for the α-carbon of the aspartate residue in the sweetener S,S-aspartame. Considering that S,S- and R,S-aspartame possess sweet and bitter tastes, respectively, a bitter-sweet taste of aza-aspartame 9 could be indicative of a low isomerization barrier for nitrogen chirality inter-conversion. Aza-aspartame 9 was synthesized by a combination of hydrazine and peptide chemistry. Crystallization of 9 indicated a R,S-configuration in the solid state; however, the aza-residue chiral center was considerably flattened relative to its natural amino acid counterpart. On tasting, the authors considered aza-aspartame 9 to be slightly bitter or tasteless. The lack of bitter sweet taste of aza-aspartame 9 may be due to flattening from sp2 hybridization in the urea as well as a high barrier for sp3 nitrogen inter-conversion, both of which may interfere with recognition by taste receptors. |
| first_indexed | 2024-12-21T22:14:10Z |
| format | Article |
| id | doaj.art-889000b3ae3446849862917610680dc8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T22:14:10Z |
| publishDate | 2013-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-889000b3ae3446849862917610680dc82022-12-21T18:48:29ZengMDPI AGMolecules1420-30492013-11-011812147391474610.3390/molecules181214739molecules181214739Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-AspartameSamir H. Bouayad-Gervais0William D. Lubell1Département de chimie, Université de Montréal, 2900 Boul. Edouard-Monpetit, Montréal, QC H3T 1J4, CanadaDépartement de chimie, Université de Montréal, 2900 Boul. Edouard-Monpetit, Montréal, QC H3T 1J4, CanadaThe potential for dynamic chirality of an azapeptide nitrogen was examined by substitution of nitrogen for the α-carbon of the aspartate residue in the sweetener S,S-aspartame. Considering that S,S- and R,S-aspartame possess sweet and bitter tastes, respectively, a bitter-sweet taste of aza-aspartame 9 could be indicative of a low isomerization barrier for nitrogen chirality inter-conversion. Aza-aspartame 9 was synthesized by a combination of hydrazine and peptide chemistry. Crystallization of 9 indicated a R,S-configuration in the solid state; however, the aza-residue chiral center was considerably flattened relative to its natural amino acid counterpart. On tasting, the authors considered aza-aspartame 9 to be slightly bitter or tasteless. The lack of bitter sweet taste of aza-aspartame 9 may be due to flattening from sp2 hybridization in the urea as well as a high barrier for sp3 nitrogen inter-conversion, both of which may interfere with recognition by taste receptors.http://www.mdpi.com/1420-3049/18/12/14739azapeptidepeptide mimicaspartamedynamic chiralityhydrazinetastecrystal structurenitrogen chiralitysemicarbazide |
| spellingShingle | Samir H. Bouayad-Gervais William D. Lubell Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame Molecules azapeptide peptide mimic aspartame dynamic chirality hydrazine taste crystal structure nitrogen chirality semicarbazide |
| title | Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame |
| title_full | Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame |
| title_fullStr | Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame |
| title_full_unstemmed | Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame |
| title_short | Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame |
| title_sort | examination of the potential for adaptive chirality of the nitrogen chiral center in aza aspartame |
| topic | azapeptide peptide mimic aspartame dynamic chirality hydrazine taste crystal structure nitrogen chirality semicarbazide |
| url | http://www.mdpi.com/1420-3049/18/12/14739 |
| work_keys_str_mv | AT samirhbouayadgervais examinationofthepotentialforadaptivechiralityofthenitrogenchiralcenterinazaaspartame AT williamdlubell examinationofthepotentialforadaptivechiralityofthenitrogenchiralcenterinazaaspartame |