Neotame: Synthesis, stereochemistry and sweetness

Article abstract of DOI:10.1080/00397919908086610

Neotame, an alkylated dipeptide-consisting of L,L-stereochemistry, is a new high intensity sweetener being developed by the Nutrition and Consumer Products Sector of Monsanto. The three diastereoisomers of neotame, L,D; D,L; and D,D were synthesized and evaluated for sweetness by sensory testing. Only the L,L-isomer was found to be sweet. The three-dimensional structure of the L,L diastereoisomer determined from single-crystal x-ray analysis demonstrates that the compound exists in an 'L shaped' conformation, previously proposed for the requirement of the sweetness ability by aspartyl- based dipeptide compounds. The confirmation of neotame in the solid state also demonstrates well-oriented hydrophobic and hydrophilic regions which likely account for the high sweetness intensity of this dipeptide compound.

Full text of DOI:10.1080/00397919908086610

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Synthetic Communications: An
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Neotame: Synthesis,
Stereochemistry and Sweetness
a
a
a
Indra Prakash , Ihab Bishay & Steve Schroeder
a
The Monsanto Company Nutrition & Consumer Sector , 601
E. Kensington Road Mount Prospect, Illinois, 60056
Published online: 25 Sep 2007.
To cite this article: Indra Prakash , Ihab Bishay & Steve Schroeder (1999) Neotame:
Synthesis, Stereochemistry and Sweetness, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 29:24, 4461-4467, DOI:
10.1080/00397919908086610
To link to this article: http://dx.doi.org/10.1080/00397919908086610
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