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MINIMAL SIDE-CHAIN PROTECTION CAN BE A SUCCESSFUL STRATEGY IN SOLID-PHASE PEPTIDE SYNTHESIS
| Content Provider | Scilit |
|---|---|
| Author | Coy, David H. Branyas, Nancy |
| Copyright Year | 2009 |
| Description | Journal: International journal of peptide and protein research The N-terminal tyrosine residue of Met-enkephalin could be readily incorporated without protection of its phenolic hydroxylgroup. Furthermore, the HF-cleaved product contained fewer impurities than that derived from hydroxyl-protected material. Despite the presence of Tyr in the center of the chain, an LH-RH antagonist, [D-Phe2, D-Trp3, D-Phe6]-LH-RH, could also be made in normal yield by incorporation of free Boc-Tyr. Syntheses of the same model peptide without protection of the Ser residue and protection of the Arg residue as the guanidine HCl salt also gave excellent yields of analog. Finally, the LH-RH inhibitor and a highly active agonist, [D-Leu6, desGly-NH2(10)]-LH-RH ethylamide, were synthesized without protection of Tyr, Ser and Arg, which enabled free peptides to be generated directly by ammonolysis and ethylaminolysis, respectively, without HF treatment. In all examples, no evidence emerged to suggest reaction of side-chains during synthesis. |
| Related Links | http://onlinelibrary.wiley.com/doi/10.1111/j.1399-3011.1979.tb01941.x/pdf |
| Ending Page | 343 |
| Page Count | 5 |
| Starting Page | 339 |
| ISSN | 03678377 |
| DOI | 10.1111/j.1399-3011.1979.tb01941.x |
| Journal | International journal of peptide and protein research |
| Issue Number | 4 |
| Volume Number | 14 |
| Language | English |
| Publisher | Wiley-Blackwell |
| Publisher Date | 2009-01-12 |
| Access Restriction | Open |
| Subject Keyword | Journal: International journal of peptide and protein research Organic Chemistry Lh‐rh Analogs Minimal Side‐chain Protection Solid‐phase Synthesis |
| Content Type | Text |
| Resource Type | Article |
| Subject | Biochemistry |
