Peptide. XI. Synthese eines Heptapeptids mit modifizierter potentieller Circulin B‐Sequenz

Abstract

Aus dem Tripeptid‐hydrazid Boc‐Lys(Z)‐aThr‐Lys(Z)‐NHNH2 9 [2] und dem Tetrapeptid aThr‐Lys(Z)‐Lys(Z)‐D‐Leu‐OMe wird durch Kupplung nach der Azid‐Methode das geschützte Heptapeptid Boc‐Lys(Z)‐aThr‐Lys (Z)‐aThr‐Lys(Z)‐Lys(Z)‐D‐Leu‐OMe 10 dargestellt. Es entspricht einer Teilsequenz das Peptidantibiotikums Circulin B, in der die α,γ‐Diaminobuttersäure durch Lysin und außerdem das Threonin durch das diastereomere Allothreonin ersetzt ist.

N-(2-Oxo-3-oxetanyl)carbamic Acid Esters as N-Acylethanolamine Acid Amidase Inhibitors: Synthesis and Structure–Activity and Structure–Property Relationships

“…(2R,3R)-allo-2-tert-Butoxycarbonylamino-3-hydroxybutyric Acid (22c): 49 (26). To a stirred suspension of NaHCO 3 (0.622 g, 7.4 mmol) in THF (1.6 mL) and H 2 O (3.3 mL) was carefully added 20b (0.353 g, 2.96 mmol).…”

“…(2R,3R)-allo-2-tert-Butoxycarbonylamino-3-hydroxybutyric Acid (22c): 49 74 Stock solutions of compounds were prepared in DMSO, and each sample was incubated at a final concentration of 1−100 μM in a prewarmed (37°C) buffer solution; the final DMSO concentration in the samples was kept at 1%. The samples were maintained at 37°C in a temperature-controlled shaking water bath (60 rpm).…”

“…37 The synthesis of threonine β-lactones 23a, 43 23b, 24a, 44 24b, 33 24c, and 24d is illustrated in Scheme 2. The amino groups of L-, D-, L-allo-, and D-allo-threonine (20a−d, respectively) were protected with 12 or di-tert-butyl dicarbonate (Boc 2 O) in aqueous sodium bicarbonate to give 21a, 45 21b, 46 22a, 47 22b, 48 22c, 49 and 22d, 50 respectively, employing a slightly modified literature procedure. 51 Cyclization to β-lactones 23a,b and 24a−d was accomplished by treating the parent compounds 21a,b and 22a−d, respectively, with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) by means of a literature procedure.…”