Labeling of DNA via rearrangement of S-2-aminoethyl phosphorothioates to N-(2-mercaptoethyl)phosphoramidates.

نویسندگان

  • Menglin Chen
  • Kurt V Gothelf
چکیده

The reaction of phosphorothioates in DNA with 2-bromoethylammonium bromide results in S-2-aminoethyl phosphorothioates, which can rearrange to N-(2-mercaptoethyl)phosphoramidates providing a facile method for the generation of site-specific thiol labeling of DNA sequences. The applicability of this method was demonstrated by conjugation of the thiolated DNA sequence with Na-(3-maleimidylpropionyl) biocytin and Alexa Fluor 546 C5-maleimide.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Two novel dATP analogs for DNA photoaffinity labeling.

Two new photoreactive dATP analogs, N(6)-[4-azidobenzoyl-(2-aminoethyl)]-2'-deoxyadenosine-5'-triphospha+ ++ te (AB-dATP) and N(6)-[4-[3-(trifluoromethyl)-diazirin-3-yl]benzoyl-(2-aminoethyl) ]-2 '-deoxyadenosine-5'-triphosphate (DB-dATP), were synthesized from 2'-deoxyadenosine-5'-monophosphate in a six step procedure. Synthesis starts with aminoethylation of dAMP and continues with rearrangem...

متن کامل

Modulation of the electronic structure and the Ni-Fe distance in heterobimetallic models for the active site in [NiFe]hydrogenase.

Reaction of the mononuclear Ni(II) thiolate complexes [Ni(L)] [L, L(1), H2L(1), bis(2-mercaptoethyl)-1,2-dimercaptoethane; L(2), H2L(2), N,N'-dimethyl-N,N'-bis(2-mercaptoethyl)-bis(aminoethyl)sulfide] with [FeCp(CO)2I] gives the dithiolate-bridged heterobimetallic species, [Ni(L(1))FeCp(CO)]PF6, 1, and [Ni(L(2))FeCp]I, 2, respectively. Binding of a Fe(CO)3 fragment via reaction of square-planar...

متن کامل

Thiol-redox antioxidants protect against lung vascular endothelial cytoskeletal alterations caused by pulmonary fibrosis inducer, bleomycin: Comparison between classical thiol protectant, N-acetyl-L-cysteine (NAC) and novel thiol antioxidant, N-N’bis-2- mercaptoethyl isophthalamide (NBMI)

Lung vascular alterations and pulmonary hypertension associated with oxidative stress have been reported to be involved in the idiopathic lung fibrosis (ILF). Therefore, here, we hypothesize that the widely used lung fibrosis inducer, bleomycin, would cause cytoskeletal rearrangement through thiol-redox alterations in the cultured lung vascular endothelial cell (EC) monolayers. We exposed the m...

متن کامل

Phosphonate–Phosphinate Rearrangement

LiTMP metalated dimethyl N-Boc-phosphoramidates derived from 1-phenylethylamine and 1,2,3,4-tetrahydronaphthalen-1-ylamine highly selectively at the CH3O group to generate short-lived oxymethyllithiums. These isomerized to diastereomeric hydroxymethylphosphonamidates (phosphate–phosphonate rearrangement). However, s-BuLi converted the dimethyl N-Boc-phosphoramidate derived from 1-phenylethylami...

متن کامل

Synthesis and characterization of poly(S-2-mercaptoethyl 2-(thiophen-3-yl)ethanethioate) by electrochemical polymerization

A novel monomer of S-2-mercaptoethyl 2-(thiophen-3-yl)ethanethioate (MTE) were synthesized via esterification reaction between 2-(thiophen-3-yl)acetic and ethane-1,2-dithiol in the presence of dicyclohexyl-carbodiimide (DCC) and N,N’-dimethylpyridin-4-amine (4-DMAP) as catalytic system. The structure of monomer was characterized via MS, 1H-NMR and 13C-NMR spectroscopies. The electrochemical pol...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 6 5  شماره 

صفحات  -

تاریخ انتشار 2008