Synthesis of biotin-containing phosphoramidite linker with polyether spacer arm

A phosphoramidite linker unit, based on glycerol backbone and containing a biotin residue attached through a tetraethylene glycol spacer arm, was synthesized. DMTr-Glycidol and tetraethylene glycol were used as starting materials. After conversion of one of hydroxy groups in tetraethylene glycol into an amino group, the epoxy cycle in DMTr-glycidol was opened by this amino alcohol, resulting in the corresponding ether and some quantity of secondary amine. After attaching of biotin residue to the ether followed by phosphitylation, the desirable linker was obtained. The structure of the linker was confirmed by1H-1H COSY,1H-13C HSQC,1H-13C HMBC,1H-15N HSQC, and1H-15N HMBC spectra. The resulted phosphoramidite linker unit is suitable for use in common DNA synthesizers. This approach can be used for preparation of various modifiers containing reporter groups attached to the primary amino function using conventional procedures. Copyright © Taylor and Francis Group, LLC.

Kayushin A, Demekhina A, Korosteleva M, Miroshnikov A, Azhayev A

IBCH: 73
Ссылка на статью в журнале: http://www.tandfonline.com/doi/abs/10.1080/15257770.2011.587702
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