Synthesis and tastant properties of disulfamates. Multisulfamation studies

Twenty four disulfamates, one trisulfamate, two tetrasulfamates and two mon osulfamates have been made. The disulfamates are of two types: RN(SO3Na)(2) (Type A, compounds 1-20) and NaO3S(H)NR'N(H)SO3Na (Type B, compounds 21-24 ) and all except three (which had not been tasted) are new materials. The p ositions of the -SO3Na groups in compounds 21-23 have been established by t he use of model compounds (e.g. parent amines, appropriate monosulfamates) and C-13-NMR. Some multisulfamation synthesis leading to compounds 25-27 ha s been carried out. Taste data have been obtained for almost all the sulfam ates made and the significance of these in relation to structure-taste stud ies for sulfamate sweeteners is discussed. In particular, the possibility t hat the entity > CHN(R)SO3- might function as a hydrogen source in the Shal lenberger-Acree, multicomponent attachment and alpha -helical protein recep tor mechanisms has been examined.