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Synthesis of C-11 linked active ester derivatives of vitamin D3 and their conjugations to 42-residue helix–loop–helix peptides
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
2010 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 25, 4577-4586 p.Article in journal (Refereed) Published
Abstract [en]

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.
National Category
Chemical Sciences
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-125724DOI: 10.1016/j.tet.2010.04.051ISI: 000278947100025OAI: oai:DiVA.org:uu-125724DiVA: diva2:320795
Available from: 2011-01-04 Created: 2010-05-27 Last updated: 2017-12-12Bibliographically approved

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Norberg, ThomasBergquist, Jonas

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