Synthesis and tastant properties of disulfamates. Multisulfamation studies

Abstract

Twenty four disulfamates, one trisulfamate, two tetrasulfamates and two monosulfamates 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 positions of the –SO₃Na groups in compounds 21–23 have been established by the use of model compounds (e.g. parent amines, appropriate monosulfamates) and ¹³C-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)SO₃⁻ might function as a hydrogen source in the Shallenberger–Acree, multicomponent attachment and α-helical protein receptor mechanisms has been examined.