title: Synthesis of biotin-containing phosphoramidite linker with polyether spacer arm.
abstract: 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 by (1)H-(1)H COSY, (1)H-(13)C HSQC, (1)H-(13)C HMBC, (1)H-(15)N HSQC, and (1)H-(15)N 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.
authors: Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia. kaushin@mail.ibch.ru
authors: Alexey
authors: A
authors: Kayushin
authors: Alexandra
authors: A
authors: Demekhina
authors: Maria
authors: M
authors: Korosteleva
authors: Anatoly
authors: A
authors: Miroshnikov
authors: Alex
authors: A
authors: Azhayev
mesh_terms: D001710:Biotin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D019855:Ethylene Glycol / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000737:chemistry
chemical_list: D009943:Organophosphorus Compounds; D011108:Polymers; C098492:biotin phosphoramidite; D001710:Biotin; D019855:Ethylene Glycol; D005990:Glycerol