To create a novel amino acid incorporating both acidic and aromatic features, trimethyltin azide was used to synthesize l-4-(tetrazol-5-yl)-phenylalanine (Tpa) and the corresponding d,l racemate by [3+2] cycloadditition of azide to the nitrile group of corresponding 4-cyanophenylalanine analogs. N a
Stereospecific synthesis of 4-carboxyphenylalanine and derivatives for use in Fmoc-based solid-phase peptide synthesis
β Scribed by Wei Wang; Nihal U. Obeyesekere; John S. McMurray
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 262 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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Established methodology for the preparation of peptide thioesters requires the use of t-butoxycarbonyl chemistry owing to the lability of thioester linkers to the nucleophilic reagents used in Fmoc solid phase peptide synthesis. Both the greater ease of use and the broad applicability of the method
Cyclic ethyl orthoformate (Ceof) was utilized as a protecting group to protect the catechol hydroxyl groups of 3,4-dihydroxyphenylalanine (DOPA). This protecting group is stable to strong bases and nucleophiles, and can be removed eciently by 1 M trimethylsilyl bromide in triΒ―uoroacetic acid in the