Amino acid building blocks for efficient Fmoc solid-phase synthesis of peptides adenylylated at serine or threonine
2011 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 13, no 22, 6014-6017 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2011. Vol. 13, no 22, 6014-6017 p.
Research subject Biorganic Chemistry
IdentifiersURN: urn:nbn:se:umu:diva-114328DOI: 10.1021/ol2024696ISI: 000296756600021PubMedID: 22029258OAI: oai:DiVA.org:umu-114328DiVA: diva2:895049