Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix
| Autor: | Kondreddi Ravinder Reddy, Gangavaram V. M. Sharma, A. V. S. Sarma, Shaik Jeelani Basha, Kodeti Srinivas Reddy |
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| Rok vydání: | 2011 |
| Předmět: |
Models
Molecular Stereochemistry Organic Chemistry Static Electricity Carboxylic Acids chemistry.chemical_element Ring (chemistry) Biochemistry Oxygen Protein Structure Secondary chemistry.chemical_compound chemistry Pyran Amide Helix Physical and Theoretical Chemistry Amino Acids Peptides 3-aminopyran-2-carboxylic acid Derivative (chemistry) Electrostatic interaction Pyrans |
| Zdroj: | Organicbiomolecular chemistry. 9(23) |
| ISSN: | 1477-0539 |
| Popis: | A new β-amino acid, trans-3-aminopyran-2-carboxylic acid (APyC), was designed and synthesized from (R)-glyceraldehyde derivative and used in the synthesis of α/β-peptides in a 1 : 1 alternating pattern with d-Ala. The presence of oxygen atom at the Cβ(2)-position in APyC was envisaged to provide opportunity for additional interaction. These hybrid peptides have shown the presence of 9/11-helix through extensive NMR and MD studies. The amide protons of d-Ala, in addition to participating in 9-mr H-bonding with CO of succeeding β-residue, were also involved in additional electrostatic interaction with pyran ring oxygen of preceding β-residue, which facilitated further stabilization to the 9/11-mixed helix. The study thus results in a new 'motif' for a 9/11-helix, and the first example from a cyclic β-amino acid. |
| Databáze: | OpenAIRE |
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