1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics
1,2,3-Triazoles represent a class of heterocycles with interesting properties for application in peptide sciences since they closely resemble amide bonds while being stable to enzymatic degradation. These characteristics make 1,2,3-triazoles promising candidates as amide-bond surrogates fo...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
2013-04-01
|
| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://www.chimia.ch/chimia/article/view/5378 |
| _version_ | 1819278688310525952 |
|---|---|
| author | Ibai E. Valverde Thomas L. Mindt |
| author_facet | Ibai E. Valverde Thomas L. Mindt |
| author_sort | Ibai E. Valverde |
| collection | DOAJ |
| description |
1,2,3-Triazoles represent a class of heterocycles with interesting properties for application in peptide sciences since they closely resemble amide bonds while being stable to enzymatic degradation. These characteristics make 1,2,3-triazoles promising candidates as amide-bond surrogates
for the development of novel peptidomimetics with potentially improved biological characteristics. Despite the potential of the heterocycle as an amide-bond isoster, only few examples of triazole-based peptidomimetics can be found in the literature. With the intention to promote this new and
promising strategy for peptide modification, this review summarizes synthetic methods available for the facile preparation of ?-amino acid and ?-amino alkyne building blocks and their use for the incorporation of 1,4-disubstituted 1,2,3 triazoles into the backbone of peptides mediated
by the Cu(i)-catalyzed alkyne–azide cycloaddition (CuAAC). In addition, examples of the successful amide-to-triazole substitution in biologically active peptides are presented.
|
| first_indexed | 2024-12-24T00:15:59Z |
| format | Article |
| id | doaj.art-927eb7f59ad244d3a62c692e7ed17b39 |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-12-24T00:15:59Z |
| publishDate | 2013-04-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-927eb7f59ad244d3a62c692e7ed17b392022-12-21T17:24:43ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242013-04-0167410.2533/chimia.2013.2621,2,3-Triazoles as Amide-bond Surrogates in PeptidomimeticsIbai E. Valverde0Thomas L. Mindt1University of Basel Hospital Department of Radiology and Nuclear Medicine Division of Radiopharmaceutical Chemistry Petersgraben 4 CH-4031 Basel, SwitzerlandUniversity of Basel Hospital Department of Radiology and Nuclear Medicine Division of Radiopharmaceutical Chemistry Petersgraben 4 CH-4031 Basel, Switzerland. Thomas.Mindt@usb.ch 1,2,3-Triazoles represent a class of heterocycles with interesting properties for application in peptide sciences since they closely resemble amide bonds while being stable to enzymatic degradation. These characteristics make 1,2,3-triazoles promising candidates as amide-bond surrogates for the development of novel peptidomimetics with potentially improved biological characteristics. Despite the potential of the heterocycle as an amide-bond isoster, only few examples of triazole-based peptidomimetics can be found in the literature. With the intention to promote this new and promising strategy for peptide modification, this review summarizes synthetic methods available for the facile preparation of ?-amino acid and ?-amino alkyne building blocks and their use for the incorporation of 1,4-disubstituted 1,2,3 triazoles into the backbone of peptides mediated by the Cu(i)-catalyzed alkyne–azide cycloaddition (CuAAC). In addition, examples of the successful amide-to-triazole substitution in biologically active peptides are presented. https://www.chimia.ch/chimia/article/view/5378Amide mimicsClick chemistryCuaacPeptidomimetics1,2,3 triazoles |
| spellingShingle | Ibai E. Valverde Thomas L. Mindt 1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics CHIMIA Amide mimics Click chemistry Cuaac Peptidomimetics 1,2,3 triazoles |
| title | 1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics |
| title_full | 1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics |
| title_fullStr | 1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics |
| title_full_unstemmed | 1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics |
| title_short | 1,2,3-Triazoles as Amide-bond Surrogates in Peptidomimetics |
| title_sort | 1 2 3 triazoles as amide bond surrogates in peptidomimetics |
| topic | Amide mimics Click chemistry Cuaac Peptidomimetics 1,2,3 triazoles |
| url | https://www.chimia.ch/chimia/article/view/5378 |
| work_keys_str_mv | AT ibaievalverde 123triazolesasamidebondsurrogatesinpeptidomimetics AT thomaslmindt 123triazolesasamidebondsurrogatesinpeptidomimetics |