Synthesis of a triply phosphorylated pentapeptide from human τ-protein

Kuder, Norman ; Zelinski, Thomas ; Pathak, Tanmaya ; Seitz, Oliver ; Waldmann, Herbert (2000) Synthesis of a triply phosphorylated pentapeptide from human τ-protein Bioorganic & Medicinal Chemistry, 8 (10). pp. 2433-2439. ISSN 0968-0896

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0968-0896(00)00174-7

Abstract

Two different strategies for the synthesis of a triply phosphorylated pentapeptide are described. In both cases a monophosphorylated selectively N-deprotected tripeptide is employed as C-terminal fragment. Coupling of this building block with a C-terminally unmasked bis-phosphorylated seryl-dipeptide unexpectedly failed due to decomposition of this peptide upon activation with different coupling reagents. Instead stepwise N-terminal elongation of the peptide chain with serine derivatives and subsequent O-phosphorylation of the serine OH-groups was successful. These results indicate that assembly of multiply phosphorylated peptides from preformed multiply phosphorylated phosphopeptide building blocks in general may be problematic and that a stepwise elongation of the amino acid chain may be preferable.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:104295
Deposited On:16 Mar 2017 12:12
Last Modified:16 Mar 2017 12:12

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