Biotin Synthesis

 

 

-----Biotin Synthesis-----

 

 

Common Names: Biotin, Vitamin B7, Vitamin H

IUPAC Name: 5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

Chemical Formula:C₁₀H₁₆N₂O₃S

Information: Biotin is vitamin B and a coenzyme.Biotin is am important supplement supports cellular function, metabolism, nervous system function, and also promotes healthy skin and nail growth. Biotin can be obtained from the diet in whole grains, eggs, and dairy products. However, synthetically produced biotin is absorbed better by the body.¹
Synthesis Steps: There are a total of 11 steps in the synthesis of biotin. The reagents used in the synthesis of biotin are common reagents that can be purchased commercially. Steps 3,7, and 10 were discussed in 341-344.Step 3 of the synthesis of Biotin involves the reduction of a carboxylic acid using DIBAL-H. In step 7 the polar protic solvent tetrahydrofuran (THF) is used. In step 10 NaBH₄ in DMF is used as a reducing agent.

Functional Groups Present: Carboxylic acid (-COOH), Sulfide(-S-), Amine (-NH-).

Step 3: Step 3 of the synthesis of biotin involves the reduction of a carboxylic acid. The reduction in step 3  uses the reagent diisobutylaluminum hydride (DIBAL-H) to reduce the RCOOR' group to RCHO. The reduction agent DIBAL-H is a mild reducing agent that reacts at low temperatures. In the reduction the H:- is donated from the DIBAL-H agent to the carboxylic acid of the compound.²

Scheme 1.1: Reaction Step 3.² 

Final Product:
Scheme 1.1: Final Product Biotin.³

History: The Roche company is a health care company that specializes in producing synthetic vitamins and their derivatives. The company was founded in 1896 by Fritz-Hoffman-La Roche.The company invests over 4 billion dollars annually in pharmaceutical research and development. Roche's goal is to create products and services to prevent, diagnose and treat a variety of illnesses. The company has four pharmaceutical locations, and six diagnostic centers across the United States.³   



References

¹WebMD Vitamins and Supplements Lifestyle Guide. http://www.webmd.com/vitamins-and-supplements/lifestyle-guide-11/supplement-guide-biotin (accessed April 12, 2013).

²Smith, Janice. Organic Chemistry. Second Edition. McGraw Hill Higher Education, 2008.

³Roche Home Page. http://www.rocheusa.com/portal/usa (accessed April 12, 2013).