Invention Grant
- Patent Title: Sulfur transfer reagents for oligonucleotide synthesis
- Patent Title (中): 用于寡核苷酸合成的硫转移试剂
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Application No.: US12958348Application Date: 2010-12-01
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Publication No.: US08552175B2Publication Date: 2013-10-08
- Inventor: Andrei P. Guzaev
- Applicant: Andrei P. Guzaev
- Applicant Address: US CA San Diego
- Assignee: A.M. Chemicals, Inc.
- Current Assignee: A.M. Chemicals, Inc.
- Current Assignee Address: US CA San Diego
- Agency: Kilpatrick Townsend & Stockton LLP
- Main IPC: C07H21/00
- IPC: C07H21/00 ; C07D417/00 ; C07D513/00 ; C07D285/14 ; C07D285/08

Abstract:
The use of N-formamidino-5-amino-3H-1,2,4-dithiazole-3-thiones, 5-phenyl-3H-1,2,4-dithiazole-3-thiones, and derivatives thereof as novel, efficient sulfur-transfer reagents is disclosed. Sulfur transfer from these reagents to compounds containing a P(III) atom (e.g., triphenylphosphine, 5′-O-DMT-thymidine 2-cyanoethyl-(N,N-diisopropyl)phosphoramidite, and 5′-O-DMT-3′-O-levulinyl dithymidilyl 2-cyanoethyl phosphite), was studied in solution by 31P NMR and HPLC. The sulfur transfer from title compounds was also studied in the solid-phase synthesis of oligonucleotide phosphorothioates by phosphoramidite methods. In this application, the efficiency of the sulfur transfer reaction for 2′-deoxyoligonucleotides was better than 99.5%. The novel sulfurizing agents are synthesized, at low cost, using simple chemical methods. As opposed to many sulfur transfer reagents known in the prior art such as 1,2-benzodithiol-3-one-1,1-dioxide (Beaucage reagent) and 5-ethoxy-3H-1,2,4-dithiazole-2-one (EDIT), the sulfurizing agents disclosed herein are highly stable in solution, which increases their practical and commercial value.
Public/Granted literature
- US20110137021A1 SULFUR TRANSFER REAGENTS FOR OLIGONUCLEOTIDE SYNTHESIS Public/Granted day:2011-06-09
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