Stabilized Analogs of Thymopentin. 2. 1,2- and 3,4-Ketomethylene Pseudopeptides
| العنوان: | Stabilized Analogs of Thymopentin. 2. 1,2- and 3,4-Ketomethylene Pseudopeptides |
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| المؤلفون: | I Uchida, Smith Rl, A K Judd, C K Hiebert, R G Almquist, Waud Wr, Dousman L, Joseph I. DeGraw |
| المصدر: | Journal of Medicinal Chemistry. 40:2398-2406 |
| بيانات النشر: | American Chemical Society (ACS), 1997. |
| سنة النشر: | 1997 |
| مصطلحات موضوعية: | Magnetic Resonance Spectroscopy, Ketone, medicine.drug_class, Stereochemistry, Peptide, Spectrometry, Mass, Fast Atom Bombardment, Pentapeptide repeat, Chemical synthesis, Aminoketone, Mice, Radioligand Assay, chemistry.chemical_compound, Adjuvants, Immunologic, Drug Stability, Isomerism, Drug Discovery, Peptide synthesis, medicine, Animals, Humans, Peptide bond, Thymopentin, chemistry.chemical_classification, Ketones, chemistry, Molecular Medicine, Oligopeptides, Half-Life, medicine.drug |
| الوصف: | In this second paper in a series of three studies of stable analogs of thymopentin (Arg1-Lys2-Asp3-Val4-Tyr5), the synthesis of analogs stabilized at peptide bonds 1,2 and 3,4 via insertion of ketomethylene units is described. A tris(carbobenzyloxy)arginyl(k)norleucine pseudopeptide was synthesized and coupled to Asp-Val-Phe-resin units followed by HF cleavage to prepare Arg(k)Nle-Asp-Val-Phe analogs. Preparation of N-BOC Asp(k)Val and N-BOC Asp(k)Ala units followed by coupling to Phe- or Tyr-resin units provided resin-bound pseudotripeptide substrates for attachment of various arginyl dipeptides. Cleavage from the resin afforded 3,4-ketomethylene-stabilized pseudopeptide analogs of thymopentin. The Arg-Lys-Asp(k)Val-Phe and Arg-Lys-Asp(k)Val-Tyr analogs were more strongly bound to CEM cells than thymopentin itself. There was significant enhancement of stability in serum for the analogs, especially those containing Arg(k)Nle or Arg-NMeLys moieties at the 1,2-peptide bond. |
| تدمد: | 1520-4804 0022-2623 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f90188d4bac5df077db3b1094584a911Test https://doi.org/10.1021/jm9508043Test |
| رقم الانضمام: | edsair.doi.dedup.....f90188d4bac5df077db3b1094584a911 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15204804 00222623 |
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