Synthesis of protected derivatives and short peptides of antAib, a novel Cα-tetrasubstituted α-amino acid of the Ac5c type possessing a fused anthracene fluorophore
作者:Jean-François Lohier、Karen Wright、Cristina Peggion、Fernando Formaggio、Claudio Toniolo、Michel Wakselman、Jean-Paul Mazaleyrat
DOI:10.1016/j.tet.2006.04.055
日期:2006.6
The Nα-Boc and Nα-Fmoc protected derivatives of 2-amino-2,3-dihydro-1H-cyclopenta[b]anthracene-2-carboxylic acid (antAib), a novel fluorescent, achiral, α-amino acid, rigid analogue of the known 9-antAla and 2-antAla residues, and belonging to the class of Ciα→Ciα cyclized, Cα,α-disubstituted glycines (strong β-turn and helix inducers in peptides), were synthesized in seven steps from 1,2,4-trimethylbenzene
所述Ñ α -Boc和Ñ α -Fmoc保护的2-氨基-2,3-二氢-1衍生物ħ环戊二烯并[ b ]蒽-2-羧酸(antAib),一种新型的荧光,非手性,α氨基酸中,已知的9-antAla和2- antAla残基的刚性类似物,和属于类的ç我α →交通ç我α环化,ç α,α从1,2,4-三甲基苯分七个步骤合成了α-二取代的甘氨酸(肽中的强β-转角和螺旋诱导剂)。还描述了Boc–antAib–OEt和Boc–antAib–OH的紫外线吸收和荧光特性。短肽Boc–antAib–1–Ala–OMe,Fmoc–1–Ala–antAib–1–Ala–OMe以及Boc–Aib–antAib–1–Ala–OMe和副产物的溶液合成2提出了5-二氧杂哌嗪环-[antAib-1-Ala]作为antAib残基在C-和N-末端的偶联能力的例子。