Adenine → Biotin

HRID 1836697Notes

Reaction equation

HRID 1836697 reaction equation
N1C(N)=C2C(N=CN2)=NC=1.[OH:11][C:12]([CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]1[C@@H:26]2[C@@H:21]([NH:22][C:23]([NH:25]2)=[O:24])[CH2:20][S:19]1)=[O:13].P(N)([O-])[O-].N1C=NN=N1.II.N>N1C=NN=N1.C(#N)C>[OH:13][C:12]([CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]1[C@@H:26]2[C@@H:21]([NH:22][C:23]([NH:25]2)=[O:24])[CH2:20][S:19]1)=[O:11]

Participants

8

Reactant 5

HCID 190Adenine2×HCID 222AmmoniaHCID 807IodineHCID 20638608HCID 20638608, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 171548Biotin

Reagents, catalysts & solvents 2

HCID 178418441HCID 178418441, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

The PNA moiety was prepared by solid phase synthesis as described in Example 1 (2 μmol synthesis). In the last cycle, a normal PNA building block, having adenine as the nucleobase, was coupled on (Formula V A; wherein TR is Mmt, U is NH, u′ is 2, PG is anisoyl, and B is adenine). After eliminating the terminal Mmt group with 3% TCA, the free amino function was reacted with biotin-phosphoramidite 5 (FIG. 4b) using tetrazole as catalyst. This reaction employs an excess of the phosphorylating reagent (approx. 10-fold) as a 0.12 M solution in acetonitrile and the tetrazole (approx. 5-fold; 0.5 M in acetonitrile). After the condensation had taken place, oxidation was effected using an iodine solution (0.05 M in tetrahydrofuran/water, pyridine (7:2:1; v:v:v)). After cleaving with ammonia, 288 OD of crude product was obtained. The crude product was purified by electrophoresis through a 15% PM gel. 17.5 OD was obtained. The product was analyzed by negative ion mass spectrometry, which confirmed the calculated mass (calc. 3789.6; found 3789.8).

Workup

  1. customThe PNA moiety was prepared by solid phase synthesis
  2. customas described in Example 1 (2 μmol synthesis)
  3. customwas obtained
  4. customThe crude product was purified by electrophoresis through a 15% PM gel
  5. custom17.5 OD was obtained

Sources & evidence

ORD record
ord-542615501a134751874b844427effdc6
Source dataset
uspto-grants-2004_08
Patent number
US06777544B2

Reaction notes

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