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Cyclization studies with tetra- and pentapeptide sequences corresponding to beta-casomorphins
International Journal of Peptide and Protein Research
|June 1, 1991
Summary
Diphenyl-phosphoryl azide (DPPA) and norborn-5-ene-2,3-dicarboximidodiphenylphosphate (NDPP) improved peptide synthesis yield and purity. Other reagents like BOP and HBTU yielded unsatisfactory results for these model peptides.
Area of Science:
- Peptide Chemistry
- Organic Synthesis
Background:
- Model peptides Boc-D-Orn-Phe-D-Pro-Gly-OH and Boc-Tyr(tBu)-D-Orn-Phe-D-Pro-Gly-OH were utilized.
- Their simple structures facilitated ring formation and prevented side reactions like racemization and cyclodimerization.
Purpose of the Study:
- To investigate the impact of various coupling reagents on peptide synthesis.
- To determine the optimal reagents for maximizing yield and purity in model peptide synthesis.
Main Methods:
- Synthesis of tetrapeptide and pentapeptide sequences.
- Evaluation of coupling reagents including DPPA, NDPP, BOP, and HBTU.
- Analysis of reaction yield and product purity.
Main Results:
- Diphenyl-phosphoryl azide (DPPA) and norborn-5-ene-2,3-dicarboximidodiphenylphosphate (NDPP) demonstrated the most favorable outcomes for yield and purity.
- Powerful activating reagents such as BOP and HBTU generally yielded unsatisfactory results, with a minor exception for HBTU/DMAP in cyclopentapeptide synthesis.
Conclusions:
- DPPA and NDPP are recommended coupling reagents for synthesizing these specific model peptides efficiently.
- The choice of coupling reagent significantly influences the success of peptide synthesis, impacting yield and purity.