Novel side reaction accompanying cyclization of Glu(R1)-Glu(R2) dipeptides via lactamization of the Glu(R1) residue
| Autor: | Vadim Kublitsky, Rimma Abramovich, Vladimir Shmygarev, Oleg N. Yatskin, Vadim T. Ivanov, Olga Ksenofontova, Maxim Dubinnyi, Vladislav Deigin |
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| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Peptidomimetic Glutamine Side reaction Diketopiperazines 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Residue (chemistry) Structural Biology Drug Discovery Amino acid residue Molecular Biology Pharmacology Molecular Structure 010405 organic chemistry Organic Chemistry General Medicine Dipeptides 0104 chemical sciences Pyrrolidonecarboxylic Acid chemistry Cyclization Molecular Medicine Pyroglutamic acid |
| Zdroj: | Journal of peptide science : an official publication of the European Peptide Society. 24(4-5) |
| ISSN: | 1099-1387 |
| Popis: | A series of linear peptides with the general formula H-Glu(R1)-Glu(R2)-OH was subjected to cyclization under standard conditions. Formation of respective 2,5-diketopiperazines was accompanied by transformation of the N-terminal Glu(R1) to pyroglutamic acid residue. Even in the case R1 is an amino acid residue attached to the N-terminal γ-carboxyl group, lactamization leads to its elimination. The observed reaction has not been reported so far in the literature. Correspondingly, an alternative route to Glu(R1)-Glu(R2)-containing 2,5-diketopiperazines was applied to improve the overall yields. |
| Databáze: | OpenAIRE |
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