Synthesis of C-11 linked active ester derivatives of vitamin D3 and their conjugations to 42-residue helix–loop–helix peptides
2010 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 25, 4577-4586 p.Article in journal (Refereed) Published
Derivatives of vitamin D3 carrying an 8-carbon linker at C-11 terminating in an active ester were synthesized from commercial vitamin D3 using a disassembly- ereassembly strategy. Vitamin D3 was cleaved at the C6-C7 double bond and the ‘upper’ fragment was converted, via a series of reactions, to derivatives substituted at C-11 with an 8-carbon linker terminating in an ethyl ester. Reassembly with modified ‘lower’ fragments using Horner-Wittig olefination followed by linker ester hydrolysis and reesterification with p-nitrophenol gave C-11 substituted p-nitrophenyl esters. These vitamin D derivatives were conjugated to 42-amino acid helix-loop-helix peptides by reaction of their p-nitrophenyl esters with lysyl side-chain amino groups on the peptides. The vitamin D-peptide conjugates, being potential specific binder candidates forvitamin D-binding protein, were characterized by mass spectroscopy and CD measurements.
Place, publisher, year, edition, pages
Elsevier , 2010. Vol. 66, no 25, 4577-4586 p.
Research subject Chemistry with specialization in Organic Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-125724DOI: 10.1016/j.tet.2010.04.051ISI: 000278947100025OAI: oai:DiVA.org:uu-125724DiVA: diva2:320795