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Phosphoramidite chloride (Making DNA the hard way)

Category: Synthesis
Posted on: January 30, 2007 9:00 AM, by Molecule of the Day

The automated chemistry for making DNA uses special monomers called phosphoramidites. To make this, you have a nucleoside (a DNA base + a DMT-protected sugar - everything but the phosphate) - and couple it to a phosphoramidite chloride. Once you've made (and purified) this, it's ready to go into a DNA synthesizer.

InChI=1/C9H18ClN2OP/c1-8(2)12(9(3)4)14(10)13-7-5-6-11/h8-9H,5,7H2,1-4H3

The final product of coupling the nucleoside to the phosphoramidite chloride is what we usually call a "phosphoramidite" - sometimes just an "amidite." The reaction produces HCl as it moves along, so it's usually done in the presence of a little Hünig's base (N,N-diisopropylethylamine) to mop that up (another non-nucleophilic base, just like DBU).

InChI=1/C19H31N4O6P.CH4/c1-12(2)23(13(3)4)30(27-8-6-7-20)29-15-9-17(28-16(15)11-24)22-10-14(5)18(25)21-19(22)26;/h10,12-13,15-17,24H,6,8-9,11H2,1-5H3,(H,21,25,26);1H4/t15-,16+,17+;/m0./s1

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Comments

Oh ya, I made it :-) and I coniugated nucleosides with sugars and enother alcohols.

Posted by: Shayek | April 13, 2007 8:06 AM

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