## Abstract The removal of amino protecting groups from a series of twelve model Z‐^3)^ or TFA‐dipeptides of dehydroalanine and (Z)‐dehydrophenylalanine was investigated. During this deprotection, peptides with Δ Ala are prone to side reactions to a higher extent than those with Δ Phe. Therefore it
Synthesis of Peptides with α,β-Dehydroamino Acids, II. Synthesis oftert-Butyloxycarbonyldipeptides of Dehydroalanine and Dehydrophenylalanine
✍ Scribed by Makowski, Maciej ;Rzeszotarska, Barbara ;Kubica, Zbigniew ;Pietrzyńnski, Grzegorz
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- English
- Weight
- 397 KB
- Volume
- 1985
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Condensation of amides of Boc‐amino acids^3)^ with pyruvic acid leads to Boc‐dipeptides 1 – 3 of dehydroalanine and 1‐Boc‐5‐alkyl‐2‐methyl‐4‐oxo‐2‐imidazolidinecarboxylic acids 8 – 10. The amides, however, do not condense with phenylpyruvic acid. Boc‐dipeptides of dehydroalanine (1 – 3) and dehydrophenylalanine (4 – 7) are synthesized using (Boc)~2~O and dehydrodipeptides with a free unmasked N‐terminal amino group.
📜 SIMILAR VOLUMES
## Abstract Condensation of amides of __N__‐(benzyloxycarbonyl)‐ and __N__‐(trifluoroacetyl)amino acid with pyruvic and phenylpyruvic acid yields, in the presence of __p__‐toluenesulfonic acid as a catalyst, __N__‐(benzyloxycarbonyl)‐ and __N__‐(trifluoroacetyl)dehydro dipeptides with C‐terminal Δ
Condensation or Zand TFA-amino acid amides with 2-0x0acids. namely butanoic, 3-methylbutanoic, 4-methylpcntanoic, and (3RS)-3-methylpentanoic acid yields (in the presence of p toluenesulfonic acid as a catalyst) Z-and TFA-dipeptides with C-terminal AAbu" (1 -4). AVal (5-8), ALeu (9-11). and AIle (12