Sequence-dependent binding of dipeptides by an artificial receptor in water.
Sequence-dependent binding of dipeptides by an artificial receptor in water.
复制标题
水中人工受体对二肽的序列依赖性结合。
作者：
C. Schmuck;Daniel Rupprecht;W. Wienand
设计并观察到人工二肽受体 (1) 在缓冲水中结合去质子化的二肽 Ac-D-Ala-D-Ala-OH，K = 33,100 M(-1)，而其他二肽如 Ac-Gly-Gly-OH 或 Ac-D-Val-D-Val-OH 的结合效率较低，超过 10 倍 (K < 3000 M(-1))。有效的结合和显着的序列选择性是强静电接触和大小区分疏水相互作用相结合的结果。为了提供这样的组合，将胍基羰基吡咯阳离子连接到新型环三亚甲基取代的丙氨酸衍生物5上，以提供刚好足够大以结合甲基但不结合任何更大的烷基链的疏水性碗形空腔，从而使受体更喜欢丙氨酸而不是缬氨酸。我们描述了 1 的合成及其在紫外和荧光滴定研究中络合特性的评估。
An artificial dipeptide receptor (1) was designed and observed to bind the deprotonated dipeptide Ac-D-Ala-D-Ala-OH in buffered water with K = 33,100 M(-1), whereas other dipeptides such as Ac-Gly-Gly-OH or Ac-D-Val-D-Val-OH were bound less efficiently, by factors of more than 10 (K < 3000 M(-1)). The efficient binding and the pronounced sequence selectivity are the result of a combination of strong electrostatic contacts and size-discriminating hydrophobic interactions. To provide such a combination, a guanidiniocarbonylpyrrole cation was attached to a novel cyclotribenzylene-substituted alanine derivative 5, to provide a hydrophobic bowl-shaped cavity just large enough to bind a methyl group but not any larger alkyl chains, thus causing the receptor to prefer alanine to valine. We describe the synthesis of 1 and the evaluation of its complexation properties in UV and fluorescence titration studies.
影响因子：
15
作者：
McComas, CC;Crowley, BM;Boger, DL
通讯作者：
Boger, DL
从合成万古霉素类似物的 SAR 研究中鉴定强效广谱抗生素。
影响因子：
2.7
作者：
Ahrendt,KateriA;Olsen,JacobA;Wakao,Masahiro;Trias,Joaquim;Ellman,JonathanA
通讯作者：
Ellman,JonathanA
影响因子：
15
作者：
Crowley, BM;Boger, DL
通讯作者：
Boger, DL