Prebiotic syntheses of vitamin coenzymes:  I.  Cysteamine and 2-mercaptoethanesulfonic acid (coenzyme M).
The reaction of NH3 and SO3(2-) with ethylene sulfide is shown to be a prebiotic synthesis of cysteamine and 2-mercaptoethanesulfonic acid (coenzyme M).  A similar reaction with ethylene imine would give cysteamine and taurine.  Ethylene oxide would react with NH3 and N(CH3)3 to give the phospholipid components ethanolamine and choline.  The prebiotic sources of ethylene sulfide, ethylene imine and ethylene oxide are discussed.  Cysteamine itself is not a suitable thioester for metabolic processes because of acyl transfer to the amino group, but this can be prevented by using an amide of cysteamine.  The use of cysteamine in coenzyme A may have been due to its prebiotic abundance.  The facile prebiotic synthesis of both cysteamine and coenzyme M suggests that they were involved in very early metabolic pathways.
Miller
S L
SL
Department of Chemistry, University of California, San Diego, La Jolla 92093-0317.
Schlesinger
G
G
D001388:Aziridines / Q000737:chemistry / Q000378:metabolism; D002794:Choline / Q000737:chemistry / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003065:Coenzyme A / Q000737:chemistry / Q000378:metabolism; D003067:Coenzymes / Q000096:biosynthesis*; D003543:Cysteamine / Q000138:chemical synthesis* / Q000737:chemistry; D004983:Ethanolamines / Q000737:chemistry / Q000378:metabolism; D005027:Ethylene Oxide / Q000737:chemistry / Q000378:metabolism; D015080:Mesna / Q000138:chemical synthesis* / Q000737:chemistry
D001388:Aziridines; D003067:Coenzymes; D004983:Ethanolamines; C033132:aziridine; D003543:Cysteamine; D005027:Ethylene Oxide; D002794:Choline; D015080:Mesna; D003065:Coenzyme A