Zanotti G, Birr C, Wieland T
Int J Pept Protein Res. 1981 Aug;18(2):162-8.
Ile3-amaninamide (3-R) and its diastereomeric sulfoxide (3-S) are obtained by oxidation of the bicyclic thioether peptide 2 by hydrogen peroxide in acetic acid. 2 was prepared by an intramolecular Savige-Fontana reaction of the linear octapeptide tert.-butylester 4 whose N-terminal Boc-Hpi residue on treatment with TFA loses the Boc group and reacts under thioether formation with the released cysteine-SH. The concomitantly deprotected carboxyl terminus is coupled intramolecularly with the free amino group of the secocompound 5 using the MA or DCCI method, thus forming the homodetic peptide ring. Compounds 3-R and 3-S agree very well with analog samples in chiroptical behavior. Thioether 2 and sulfoxide 3-R exert 50% inhibition of RNA polymerase II (or B) from Drosophila melanogaster in 10(-6) M solution whereas Ki of 3-S is about five times higher.
鹅膏蕈氨酸酰胺（3 - R）及其非对映体亚砜（3 - S）是通过在乙酸中用过氧化氢氧化双环硫醚肽2得到的。2是由线性八肽叔丁酯4通过分子内萨维奇 - 丰塔纳反应制备的，其N - 末端的Boc - Hpi残基在用TFA处理时失去Boc基团，并与释放的半胱氨酸 - SH在硫醚形成反应中发生反应。同时脱保护的羧基末端使用MA或DCCI方法与二级化合物5的游离氨基进行分子内偶联，从而形成同系环肽。化合物3 - R和3 - S在手性光学行为方面与类似样品非常吻合。硫醚2和亚砜3 - R在10^(-6) M溶液中对黑腹果蝇的RNA聚合酶II（或B）有50%的抑制作用，而3 - S的Ki约高五倍。
