Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid
The reaction between L-cysteine (Cys) and 6-maleimidohexanoic acid (Mhx) in an aqueous medium at different levels of pH was analyzed via RP-HPLC, finding the presence of two reaction products throughout the evaluated pH range. By means of solid-phase extraction (SPE), it was possible to separate the...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/16/5064 |
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| author | Víctor Alfonso Niño-Ramírez Diego Sebastián Insuasty-Cepeda Zuly Jenny Rivera-Monroy Mauricio Maldonado |
| author_facet | Víctor Alfonso Niño-Ramírez Diego Sebastián Insuasty-Cepeda Zuly Jenny Rivera-Monroy Mauricio Maldonado |
| author_sort | Víctor Alfonso Niño-Ramírez |
| collection | DOAJ |
| description | The reaction between L-cysteine (Cys) and 6-maleimidohexanoic acid (Mhx) in an aqueous medium at different levels of pH was analyzed via RP-HPLC, finding the presence of two reaction products throughout the evaluated pH range. By means of solid-phase extraction (SPE), it was possible to separate the products and obtain isolated profiles enriched up to 80%. The products were analyzed individually through mass spectrometry, DAD-HPLC, NMR <sup>1</sup>H, <sup>13</sup>C, and two-dimensional evidence of isomerization between the hydrogen atoms of the α-amino and the thiol group present in the cysteine. Thus, it was concluded that the products obtained corresponded to a mixture of the isomer Cys-S-Mhx, where the adduct is formed by a thioether bond, and the isomer Cys-NH-Mhx, in which the union is driven by the amino group. We consider that the phenomenon of isomerization is an important finding, since it has not previously been reported for this reaction. |
| first_indexed | 2024-03-09T09:51:33Z |
| format | Article |
| id | doaj.art-0a0692a9e20147649d3ed0629a3d08a4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T09:51:33Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0a0692a9e20147649d3ed0629a3d08a42023-12-02T00:03:53ZengMDPI AGMolecules1420-30492022-08-012716506410.3390/molecules27165064Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic AcidVíctor Alfonso Niño-Ramírez0Diego Sebastián Insuasty-Cepeda1Zuly Jenny Rivera-Monroy2Mauricio Maldonado3Chemistry Department, Universidad Nacional de Colombia, Bogotá, Carrera 45 No 26-85, Building 451, Office 409, Bogotá 11321, ColombiaChemistry Department, Universidad Nacional de Colombia, Bogotá, Carrera 45 No 26-85, Building 451, Office 409, Bogotá 11321, ColombiaChemistry Department, Universidad Nacional de Colombia, Bogotá, Carrera 45 No 26-85, Building 451, Office 409, Bogotá 11321, ColombiaChemistry Department, Universidad Nacional de Colombia, Bogotá, Carrera 45 No 26-85, Building 451, Office 409, Bogotá 11321, ColombiaThe reaction between L-cysteine (Cys) and 6-maleimidohexanoic acid (Mhx) in an aqueous medium at different levels of pH was analyzed via RP-HPLC, finding the presence of two reaction products throughout the evaluated pH range. By means of solid-phase extraction (SPE), it was possible to separate the products and obtain isolated profiles enriched up to 80%. The products were analyzed individually through mass spectrometry, DAD-HPLC, NMR <sup>1</sup>H, <sup>13</sup>C, and two-dimensional evidence of isomerization between the hydrogen atoms of the α-amino and the thiol group present in the cysteine. Thus, it was concluded that the products obtained corresponded to a mixture of the isomer Cys-S-Mhx, where the adduct is formed by a thioether bond, and the isomer Cys-NH-Mhx, in which the union is driven by the amino group. We consider that the phenomenon of isomerization is an important finding, since it has not previously been reported for this reaction.https://www.mdpi.com/1420-3049/27/16/5064click reactionMichael additionthiol-maleimide additionisomerization |
| spellingShingle | Víctor Alfonso Niño-Ramírez Diego Sebastián Insuasty-Cepeda Zuly Jenny Rivera-Monroy Mauricio Maldonado Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid Molecules click reaction Michael addition thiol-maleimide addition isomerization |
| title | Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid |
| title_full | Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid |
| title_fullStr | Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid |
| title_full_unstemmed | Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid |
| title_short | Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid |
| title_sort | evidence of isomerization in the michael type thiol maleimide addition click reaction between l cysteine and 6 maleimidehexanoic acid |
| topic | click reaction Michael addition thiol-maleimide addition isomerization |
| url | https://www.mdpi.com/1420-3049/27/16/5064 |
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