Partially modified retro‐inverso peptides
Several synthetic routes are reported to prepare the hetero diprotected 1,1‐diaminoalkanes from N ‐acylated amino acids or peptides for incorporation into partially modified retro‐inverso peptides. The Curtius rearrangement was carried out on the N ‐protected aminoacyl azides obtained from the N ‐pr...
| Published in: | International Journal of Peptide and Protein Research |
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| Main Authors: | , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
1983
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1111/j.1399-3011.1983.tb03103.x https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fj.1399-3011.1983.tb03103.x https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1399-3011.1983.tb03103.x |
| Summary: | Several synthetic routes are reported to prepare the hetero diprotected 1,1‐diaminoalkanes from N ‐acylated amino acids or peptides for incorporation into partially modified retro‐inverso peptides. The Curtius rearrangement was carried out on the N ‐protected aminoacyl azides obtained from the N ‐protected aminoacyl hydrazide by nitrosyl chloride or by sodium azide reaction with an appropriate mixed carboxylic carbonic acid anhydride. The resulting isocyanate was allowed to react with alcohol to give a urethane‐type protecting group or, via a “one‐pot” approach, directly with a carboxyl carrying component to yield the modified (reversed) peptide bond. The carboxyl component can be either an N ‐acylated amino acid or a malonic acid. The more standard route involves selective deprotection of the 1,1‐diaminoalkane residue followed immediately by coupling with a carboxyl component to yield the same modified peptide derivative. |
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