A new series of cyclic amino acids as inhibitors of S-adenosyl L-methionine synthetase

Characterisation of methionine adenosyltransferase from Mycobacterium smegmatis and M. tuberculosis

“…For example, cycloleucine, which is often treated as a classic inhibitor of MAT activity, only has a Ki of 10 mM against human MAT [23]. Similarly, four other cyclic analogues of methionine had Ki values of 0.75–3.0 mM against rat liver MAT [38]. Of thirteen methylmethionine analogues, the best three compounds had Ki values ranging from 0.5–2.4 mM, while most had little inhibitory effect [39].…”

Practical Methods for the Synthesis of Symmetrically α,α-Disubstituted α-Amino Acids

“…The nonstereoselective synthesis of N-protected Tetrahydropyran-4-one and tetrahydrothiopyran-4-one 36 were converted into the corresponding hydantoins 37 in excellent yields (> 90%) by allowing them to react with potassium cyanide and ammonium carbonate at 50°C (Scheme 7). 27 Cyclic amino acids 38 were obtained by treatment of hydantoins 37 with barium hydroxide at 100°C for 24 hours in good yields (≥ 80%) and examined as potential inhibitors of the enzyme S-adenosylmethionine (AdoMet) synthetase.…”

A novel 2H-azirin-3-amine as a synthon for a sulfur-containing dipeptide segment

“…For example, the tetrahydro-2H-thiopyran derivative 1b (X = S, n = 1) has been used to prepare tripeptides containing 4-aminotetrahydro-2H-thiopyran-4-carboxylic acid (5) [12]. This heterocyclic amino acid has been described as a cyclic homocysteine [16] or methionine analog [17], and was prepared via Strecker synthesis [18], the Bucherer-Bergs reaction [17,19], or the Ugi reaction [20]. The crystal structure of 5 has been published in 1976 [21].…”

“…The crystal structure of 5 has been published in 1976 [21]. The interest in the amino acid 5 is based on the biological activities of some of its derivatives, e.g., as inhibitors of S-adenosyl Lmethionine synthetase [19], glycogen phosphorylase inhibitor [22], or ecdysone agonist [23].…”