Ammonia → Biotin

HRID 1836698Notes

Reaction equation

HRID 1836698 reaction equation
N1C(=O)C2NC=NC=2N=C1N.O=O.[OH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]1[C@@H:29]2[C@@H:24]([NH:25][C:26]([NH:28]2)=[O:27])[CH2:23][S:22]1)=[O:16].P(N)([O-])[O-].N1C=NN=N1.II.N>N1C=NN=N1.C(#N)C>[OH:16][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]1[C@@H:29]2[C@@H:24]([NH:25][C:26]([NH:28]2)=[O:27])[CH2:23][S:22]1)=[O:14]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 807IodineHCID 977OxygenHCID 20638608HCID 20638608, compoundHCID 135398634Guanine2×HCID 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 (1 μmol synthesis). A hydroxyethyleneglycine-based building block having guanine as the nucleobase (Formula V A; wherein TR is Dmt, U is oxygen, u′ is 2, PG is anisoyl and B is guanine) was coupled on in the last cycle. After eliminating the terminal Dmt group with 3% TCA, the free hydroxyl 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. 50-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, 63 OD of crude product was obtained. The crude product was purified by electrophoresis through a 15% PAA gel. 11.2 OD was obtained. The product was analyzed by negative ion mass spectrometry, which confirmed the calculated mass (calc. 3806.8; found 3807.2).

Workup

  1. customThe PNA moiety was prepared by solid phase synthesis
  2. customas described in Example 1 (1 μmol synthesis)
  3. customwas obtained
  4. customThe crude product was purified by electrophoresis through a 15% PAA gel
  5. custom11.2 OD was obtained

Sources & evidence

ORD record
ord-08517e3b22b4482e803cddbacb43ec0e
Source dataset
uspto-grants-2004_08
Patent number
US06777544B2

Reaction notes

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