细胞生长抑制性环四肽WF-3161，环[L-亮氨酰-L-哌啶酰-L-(2-氨基-8-氧代-9,10-环氧癸酰基)-D-苯丙氨酰基]的结构与溶液构象
Structure and solution conformation of the cytostatic cyclic tetrapeptide WF-3161, cyclo[L-leucyl-L-pipecolyl-L-(2-amino-8-oxo-9, 10-epoxydecanoyl)-D-phenylalanyl].
作者信息
Kawai M, Pottorf R S, Rich D H
出版信息
J Med Chem. 1986 Nov;29(11):2409-11. doi: 10.1021/jm00161a046.
The sequence and configuration of amino acids in the cytostatic cyclic tetrapeptide WF-3161 are established as cyclo(L-Leu-L-Pip-L-Aoe-D-Phe) where Pip = pipecolic acid and Aoe = 2-amino-8-oxo-9,10-epoxydecanoic acid. In chloroform, WF-3161 adopts a conformation with a possible gamma-turn between Leu NH and Aoe C = O and a cis amide bond between Leu and Pip. The torsion angles for this conformation are L-Aoe, phi, -95 degrees, psi, +85 degrees, omega, -155 degrees; D-Phe, phi, +120 degrees, psi, -80 degrees, omega, -175 degrees; L-Leu, phi, -145 degrees, psi, +35 degrees, omega, -10 degrees; L-Pip, phi, +20 degrees, psi, -135 degrees, omega, -170 degrees. The cis,trans,trans,trans amide bond sequence is related to the dimethyl sulfoxide conformation of chlamydocin, another cytostatic cyclic tetrapeptide.
细胞生长抑制性环四肽WF - 3161的氨基酸序列和构型确定为环（L - 亮氨酸 - L - 哌啶酸 - L - 2 - 氨基 - 8 - 氧代 - 9,10 - 环氧癸酸 - D - 苯丙氨酸），其中哌啶酸（Pip）= 哌啶酸，2 - 氨基 - 8 - 氧代 - 9,10 - 环氧癸酸（Aoe）= 2 - 氨基 - 8 - 氧代 - 9,10 - 环氧癸酸。在氯仿中，WF - 3161呈现出一种构象，在亮氨酸氨基（Leu NH）和2 - 氨基 - 8 - 氧代 - 9,10 - 环氧癸酸羰基（Aoe C = O）之间可能存在一个γ - 转角，并且亮氨酸和哌啶酸之间存在一个顺式酰胺键。该构象的扭转角为：L - 2 - 氨基 - 8 - 氧代 - 9,10 - 环氧癸酸，φ， - 95°，ψ， + 85°，ω， - 155°；D - 苯丙氨酸，φ， + 120°，ψ， - 80°，ω， - 175°；L - 亮氨酸，φ， - 145°，ψ， + 35°，ω， - 10°；L - 哌啶酸，φ， + 20°，ψ， - 135°，ω， - 170°。顺式、反式、反式、反式酰胺键序列与另一种细胞生长抑制性环四肽氯代霉素在二甲基亚砜中的构象有关。
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