Amino acid building blocks for efficient Fmoc solid-phase synthesis of peptides adenylylated at serine or threonine.
The first straightforward building block based (non-interassembly) synthesis of peptides containing adenylylated serine and threonine residues is described. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The described Thr-AMP SPPS-building block has been employed in the synthesis of the Thr-adenylylated sequence of human GTPase CDC42 (Ac-SEYVP-T(AMP)-VFDNYGC-NH(2)). Further, we demonstrate proof-of-concept for the synthesis of an Ser-adenylylated peptide (Ac-GSGA-S(AMP)-AGSGC-NH(2)) from the corresponding adenylylated serine building block.
Department of Chemical Biology, Max-Planck Institute of Molecular Physiology, Otto-Hahn Strasse 11, D-44227, Dortmund, Germany.
Michael F
MF
Albers
Bart
B
van Vliet
Christian
C
Hedberg
D000225:Adenine / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D012694:Serine / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D013912:Threonine / Q000737:chemistry
D000596:Amino Acids; D010455:Peptides; D013912:Threonine; D012694:Serine; D000225:Adenine