Production of artificial sweeteners?

[Chuck2600]

Does anyone know where I can find information regarding the actual production of artificial sweeteners (more specifically aspartame and sucralose) I need it for a paper. Despite the overwhelming amount of information on the topic there is very little about the actual production.

[Chuck2600]

Wonderpug, lol

[cls91]

Aspartame:

Aspartame is produced by coupling together L-phenylalanine (or L-phenylalanine methyl ester) and L-aspartic acid, either chemically or enzymatically. The former procedure yields both the sweet alpha-aspartame and nonsweet beta-aspartame from which the alpha aspartame has to be separated and purified. The enzymatic process yields only alpha-aspartame.

Production of aspartame normally starts from L-aspartic acid and L-phenylalanine or L-phenylalanine methyl ester. The production follows common routes of peptide synthesis, as the L-configuration of amino acids has to be retained (essential for sweetness). Common production routes require protective groups for aspartic acid. The protective groups commonly used in peptide synthesis have been suggested for aspartame synthesis, but simple protection for large-scale production can be obtained by use of formylaspartic acid anhydride. It can be reacted with phenylalanine methyl ester to N-formylaspartame, from which the protective group has to be removed. Especially simple production is possible from N-formylaspartic acid anhydride and L-phenylalanine. The resulting N-formylaspartylphenylalanine is treated with hydrochloric acid and methanol. The aspartame hydrochloride obtained can be crystallized for purification and transformed into aspartame after addition of a stoichiometric amount of a neutralizing agent. Adjustment of the solvent increases the yield by improving the ratio of alpha- to beta-isomers. Crystallization of alpha-aspartame hydrohalides is a suitable purification step, as beta-hydrohalides are more soluble.

Method for large-scale production of aspartame ... L-aspartic acid anhydride is condensed with L-phenylalanine methyl ester to form a mixture of beta-L-aspartyl-L-phenylalanine methyl ester and alpha-L-aspartyl-L-phenylalanine methyl ester. On acidification with hydrochloric acid, the latter precipitates and the precipitate is neutralized to form aspartame. /From table/

Source: http://pubchem.ncbi.nlm.nih.gov/summ...y.cgi?cid=2242




Sucralose:

Tate & Lyle currently manufactures sucralose both at a plant in Jurong, Singapore.[11] and at a recently reopened plant in McIntosh, Alabama. It is manufactured by the selective chlorination of sucrose (table sugar), which substitutes three of the hydroxyl groups with chlorine. This chlorination is achieved by selective protection of the primary alcohol groups followed by acetylation and then deprotection of the primary alcohol groups. Following an induced acetyl migration on one of the hydroxyl groups, the partially acetylated sugar is then chlorinated with a chlorinating agent such as phosphorus oxychloride, followed by removal of the acetyl groups to give sucralose.[12]

Source: http://en.wikipedia.org/wiki/Sucralose
Which is linked from: http://www.princeton.edu/~achaney/tm...Sucralose.html