No abstract

The effect of sulfamation on known tastants has been investigated using several series of compounds containing a primary amine function namely, nitroanilines, phenylureas and -thioureas and amino acids and peptides. Profund changes in taste took place on sulfamation. The effect of chirality on the taste portfolios of various sulfamates has also been examined by preparing sets of enantiomeric pairs from aliphatic, aliphatic/aromatic and alicyclic/aromatic precursor amines and aminoalcohols. Some interesting taste differences have emerged, though these are not as great as observed in the first study.530

Twenty four disulfamates, one trisulfamate, two tetrasulfamates and two monosulfamates have been made. The disulfamates are of two types: RN(SO 3 Na) 2 (Type A, compounds 1-20) and NaO 3 S(H)NRЈN(H)SO 3 Na (Type B, compounds 21-24) and all except three (which had not been tasted) are new materials. The positions of the -SO 3 Na groups in compounds 21-23 have been established by the use of model compounds (e.g. parent amines, appropriate monosulfamates) and 13 C-NMR. Some multisulfamation synthesis leading to compounds 25-27 has been carried out. Taste data have been obtained for almost all the sulfamates made and the significance of these in relation to structure-taste studies for sulfamate sweeteners is discussed. In particular, the possibility that the entity CHN(R)SO 3 Ϫ might function as a hydrogen source in the Shallenberger-Acree, multicomponent attachment and α-helical protein receptor mechanisms has been examined.

2001 amines amines (acyclic compounds) P 0060 17 -079 Synthesis and Tastant Properties of Disulfamates. Multisulfamation Studies. -Structure-taste studies on twenty-nine sulfamates, e.g. (I)-(III), reveal the absence of sweetness in all disulfamates, which contain the entity =CHN(SO 3 Na) 2 . This absence of sweetness underlines the necessity for an imino hydrogen in the sulfamate functionality as in (III) that can actively participate in hydrogen bonding in the dual H-bond theory of Shallenberger and Acree. Additional doubt appears on 1974 report that sulfamates containing the entity =CHN(R)SO 3 − are sweet. -(SPILLANE, WM. J.; RYDER, CAROLINE A.; CONCAGH, DANNY G.; KELLY, LORRAINE M.; Perkin 2 (2001) 1, 103-107; Chem. Dep., Nat. Univ. Ire., Galway, Ire.; EN)