Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups
Abstract A synthesis of new enantiomerically enriched derivatives of (S)-α-aminopropionic acid, containing in the β-position 1,2,3-triazole groups coupled with a o-, m- and p-substituted phenyl residue, was developed based on Cu(I) catalyzed [3 + 2] cycloaddition of azides with alkynes. As the start...
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| Format: | Article |
| Language: | English |
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Springer
2024-12-01
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| Series: | Amino Acids |
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| Online Access: | https://doi.org/10.1007/s00726-024-03430-5 |
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| author | Artavazd S. Poghosyan Emma A. Khachatryan Anna F. Mkrtchyan Volodya Mirzoyan Anahit M. Hovhannisyan Karapet R. Ghazaryan Ela V. Minasyan Peter Langer Ashot S. Saghyan |
| author_facet | Artavazd S. Poghosyan Emma A. Khachatryan Anna F. Mkrtchyan Volodya Mirzoyan Anahit M. Hovhannisyan Karapet R. Ghazaryan Ela V. Minasyan Peter Langer Ashot S. Saghyan |
| author_sort | Artavazd S. Poghosyan |
| collection | DOAJ |
| description | Abstract A synthesis of new enantiomerically enriched derivatives of (S)-α-aminopropionic acid, containing in the β-position 1,2,3-triazole groups coupled with a o-, m- and p-substituted phenyl residue, was developed based on Cu(I) catalyzed [3 + 2] cycloaddition of azides with alkynes. As the starting materials was used the square-planar Ni(II)complex of the Schiff base of propargylglycine with the chiral auxiliary BPB (Benzylprolylbenzophenone) and 1,4-substituted phenyl azides. The assignment of the (S)-absolute configuration of the α-carbon atom of the amino acid residue of the main diastereomeric complexes of the cycloaddition products was carried out on the basis of positive Cotton effects in the region of 480–580 nm of the circular dichroism spectra. The target amino acids were isolated from acid hydrolysates of diastereomeric complexes using ion-exchange demineralization and crystallization from aqueous ethanol. Additional confirmation of the absolute configuration and determination of the enantiomeric purity of the target amino acids were carried out by chiral HPLC analysis. As a result, seven new non-proteinogenic (S)-α-amino acids, containing in the β-position a 1,2,3-triazole moiety, were synthesized. |
| format | Article |
| id | doaj-art-bd7bd1d4698047169d78fae3744ced08 |
| institution | OA Journals |
| issn | 1438-2199 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Springer |
| record_format | Article |
| series | Amino Acids |
| spelling | doaj-art-bd7bd1d4698047169d78fae3744ced082025-08-20T01:57:16ZengSpringerAmino Acids1438-21992024-12-0156111110.1007/s00726-024-03430-5Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groupsArtavazd S. Poghosyan0Emma A. Khachatryan1Anna F. Mkrtchyan2Volodya Mirzoyan3Anahit M. Hovhannisyan4Karapet R. Ghazaryan5Ela V. Minasyan6Peter Langer7Ashot S. Saghyan8Scientific and Production Center “Armbiotechnology” of NAS RAInstitute of Pharmacy, Yerevan State UniversityScientific and Production Center “Armbiotechnology” of NAS RAInstitute of Pharmacy, Yerevan State UniversityInstitute of Pharmacy, Yerevan State UniversityScientific and Production Center “Armbiotechnology” of NAS RAScientific and Production Center “Armbiotechnology” of NAS RAInstitute of Chemistry, Organic Chemistry, University of RostockScientific and Production Center “Armbiotechnology” of NAS RAAbstract A synthesis of new enantiomerically enriched derivatives of (S)-α-aminopropionic acid, containing in the β-position 1,2,3-triazole groups coupled with a o-, m- and p-substituted phenyl residue, was developed based on Cu(I) catalyzed [3 + 2] cycloaddition of azides with alkynes. As the starting materials was used the square-planar Ni(II)complex of the Schiff base of propargylglycine with the chiral auxiliary BPB (Benzylprolylbenzophenone) and 1,4-substituted phenyl azides. The assignment of the (S)-absolute configuration of the α-carbon atom of the amino acid residue of the main diastereomeric complexes of the cycloaddition products was carried out on the basis of positive Cotton effects in the region of 480–580 nm of the circular dichroism spectra. The target amino acids were isolated from acid hydrolysates of diastereomeric complexes using ion-exchange demineralization and crystallization from aqueous ethanol. Additional confirmation of the absolute configuration and determination of the enantiomeric purity of the target amino acids were carried out by chiral HPLC analysis. As a result, seven new non-proteinogenic (S)-α-amino acids, containing in the β-position a 1,2,3-triazole moiety, were synthesized.https://doi.org/10.1007/s00726-024-03430-5Enantiomerically enriched amino acid[3 + 2] cycloadditionChiral BPBNi(II) square-planar complexes |
| spellingShingle | Artavazd S. Poghosyan Emma A. Khachatryan Anna F. Mkrtchyan Volodya Mirzoyan Anahit M. Hovhannisyan Karapet R. Ghazaryan Ela V. Minasyan Peter Langer Ashot S. Saghyan Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups Amino Acids Enantiomerically enriched amino acid [3 + 2] cycloaddition Chiral BPB Ni(II) square-planar complexes |
| title | Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups |
| title_full | Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups |
| title_fullStr | Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups |
| title_full_unstemmed | Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups |
| title_short | Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups |
| title_sort | synthesis of enantiomerically enriched β substituted analogs of s α alanine containing 1 phenyl 1h 1 2 3 triazole groups |
| topic | Enantiomerically enriched amino acid [3 + 2] cycloaddition Chiral BPB Ni(II) square-planar complexes |
| url | https://doi.org/10.1007/s00726-024-03430-5 |
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