6-(5-Methyl-2-oxoimidazolidin-4-yl)hexanoic acid → Biotin

HRID 278841Notes

Reaction equation

HRID 278841 reaction equation
[CH3:1][CH:2]1[NH:7][C:5](=[O:6])[NH:4][CH:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].N[C@H](C(O)=O)C[SH:19].C(S)[C@@H](O)[C@H](O)CS.C(O)C(N)(CO)CO.Cl>>[OH:14][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[C@@H:3]2[C@@H:2]([NH:7][C:5]([NH:4]2)=[O:6])[CH2:1][S:19]1)=[O:15]

Participants

5

Reactant 4

HCID 6436-(5-Methyl-2-oxoimidazolidin-4-yl)hexanoic acidHCID 5862L-(+)-CysteineHCID 93573Tromethamine hydrochlorideHCID 446094D-1,4-Dithiothreitol

Product 1

HCID 171548Biotin

Conditions

Temperature
95 °C

Procedure

The enzyme reaction mixture without cell-free extracts contained 100 μM desthiobiotin. 1000 μM SAM, 200 μM L-cysteine, 50 μM deazariboflavin, 0.6 mg/ml (16 μM) BIOB protein, 10 mM DTT and 0.1 M Tris-HCl/pH 7.5 in total volume of 50 μl. The enzyme reaction mixture in a 300 μl glass spitz tube was brought to anaerobic condition by repeating of weak aspiration and argon pressure under dark. The reaction was started by light irradiation from 10 cm distance with 20 W fluorescent bulb at 30° C. After 80 min reaction, reaction was stopped by heating at 95° C., and produced biotin was determined by the microbiological assay 1 ) using Lactobacillis plantarum. (ATCC8014)

Workup

  1. customThe enzyme reaction mixture without cell-free extracts
  2. customThe enzyme reaction mixture in a 300 μl glass spitz tube
  3. customThe reaction was started by light irradiation from 10 cm distance with 20 W fluorescent bulb at 30° C
  4. customAfter 80 min reaction, reaction

Sources & evidence

ORD record
ord-22f08647252b41f3a5c4a7ae36be25b5
Source dataset
uspto-grants-2002_03
Patent number
US06361978B1

Reaction notes

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