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Solid-phase peptide synthesis using tert.-butyloxycarbonylamino acid pentafluorophenyl esters
L Otvos1, B Dietzschold, L Kisfaludy
1Wistar Institute of Anatomy and Biology, Philadelphia, Pennsylvania.
International Journal of Peptide and Protein Research
|October 1, 1987
Summary
Boc-amino acid pentafluorophenyl esters are effective for solid-phase peptide synthesis, offering comparable coupling rates and product purity to symmetrical anhydrides. These active esters necessitate specific conditions like modified Merrifield resin and polar solvents.
Area of Science:
- Organic Chemistry
- Biochemistry
- Synthetic Chemistry
Background:
- Solid-phase peptide synthesis (SPPS) is a crucial technique for creating peptide chains.
- Traditional coupling reagents like symmetrical anhydrides have limitations.
- Developing efficient and reliable active esters is vital for advancing SPPS.
Purpose of the Study:
- To evaluate the efficacy of Boc-amino acid pentafluorophenyl esters in SPPS.
- To compare their performance against established coupling methods.
- To identify optimal conditions for using these active esters.
Main Methods:
- Utilized Boc-amino acid pentafluorophenyl esters for peptide coupling.
- Employed modified Merrifield resin.
- Conducted coupling reactions in a polar medium, with and without base catalysis.
Main Results:
- Achieved successful peptide synthesis using the active esters.
- Demonstrated coupling rates comparable to symmetrical anhydrides.
- Obtained high purity of synthesized peptide products.
Conclusions:
- Boc-amino acid pentafluorophenyl esters represent a viable alternative for SPPS.
- Their effectiveness is comparable to symmetrical anhydrides.
- Specific reaction conditions, including resin modification and polar solvents, are key for optimal performance.