| Autor: |
J, Hiebl, D P, Alberts, A F, Banyard, K, Baresch, H, Baumgartner, I, Bernwieser, P K, Bhatnagar, M, Blanka, M, Bodenteich, T, Chen, P M, Esch, H, Kollmann, I, Lantos, K, Leitner, G, Mayrhofer, R, Patel, A, Rio, F, Rovenszky, D, Stevenson, K D, Tubman, K, Undheim, H, Weihtrager, W, Welz, K, Winkler |
| Rok vydání: |
1999 |
| Předmět: |
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| Zdroj: |
The journal of peptide research : official journal of the American Peptide Society. 54(1) |
| ISSN: |
1397-002X |
| Popis: |
Linear and convergent routes for the large-scale preparation of the hematoregulatory nonapeptide (Glp-Glu-Asp)2-DAS-(Lys)2 (2, SKF 107647) were investigated. A convergent approach ('3 + 2'-route employing Boc-and benzyl ester protecting groups) was selected for the preparation of multihundred-gram quantities of 2. Key steps were the preparation and the coupling of tripeptide hydrochloride (HCl.H)2-DAS-(Lys(Z)-OBn)2 (6, DAS-2,7-L,L-diaminosuberic acid) and tripeptide Glp-Glu(OBn)-Asp(OBn)-OH (26). Several coupling reagents were investigated in order to reduce the amount of epimerization of this fragment coupling. TDBTU [O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl-1,1,3,3-tetrameth yluronium tetrafluoroborate] was identified as the condensation reagent of choice. Using this synthetic route97% pure final product in an overall yield of 35% calculated on di-Boc protected 2,7-L,L-diaminosuberic acid was prepared. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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