Stereomeric resolution and modeling of DL-alanine-DL-phenyl alanine dipeptide on an AmyCoat-RP column,Analytical Methods

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Stereomeric resolution and modeling of DL-alanine-DL-phenyl alanine dipeptide on an AmyCoat-RP column
Analytical Methods ( IF 2.7 ) Pub Date : 2019-11-18 , DOI: 10.1039/c9ay02226k
Nora Hamad Al-Shaalan _{1,

2,

3,

4,

5} , Imran Ali _{1,

1,

5,

6,

7} , Zeid A. ALOthman _{1,

2,

5,

8,

9} , Lamya Hamad Al-Wahaibi _{1,

2,

3,

4,

5} , Hadeel Alabdulmonem _{1,

2,

3,

4,

5}

Affiliation

Stereomeric resolution and docking studies of four stereomers of DL-alanine-DL-phenyl alanine dipeptide were performed with an AmyCoat-RP column. The eluent used was methanol : ammonium acetate (10 mM) : formic acid (70 : 30 : 0.05, v/v) with 0.8 mL min⁻¹ flow rate, 275 nm detection and 27 ± 2 °C temperature. The values of retention factors for LL-, DD-, DL- and LD-stereomers were 1.36, 2.21, 8.63 and 11.3. The values of separation factors were 1.63, 3.91 and 1.31. The values of resolution factors were 1.70, 6.43 and 2.14, respectively. The detection and quantitation limits were 0.62–1.43 and 3.10–10.0 ng. The docking studies have proven the order of elution and the stereomeric mechanism. The different forces responsible for stereomeric resolution were hydrogen bonding, hydrophobic interactions, π–π forces, van der Waals attractions, and steric effects. The described stereomeric resolution of the reported racemic dipeptide is highly useful. It may be used to access the quantities of various stereomeric compounds in any unknown matrix.

中文翻译：

AmyCoat-RP色谱柱上DL-丙氨酸-DL-苯丙氨酸二肽的立体异构拆分和建模

用AmyCoat-RP色谱柱进行了DL-丙氨酸-DL-苯基丙氨酸二肽的四种立体异构体的立体异构拆分和对接研究。所用的洗脱液为甲醇：乙酸铵（10 mM）：甲酸（70：30：0.05，v / v），流速为0.8 mLmin ^-1，检测波长为275 nm，温度为27±2°C。LL-，DD-，DL-和LD的保留因子值-立体异构体分别为1.36、2.21、8.23和11.3。分离因子的值为1.63、3.91和1.31。分辨率因子的值分别为1.70、6.43和2.14。检出限和定量限为0.62-1.43和3.10-10.0 ng。对接研究已证明洗脱顺序和立体异构机理。引起立体异构体拆分的不同力是氢键，疏水相互作用，π–π力，范德华力和空间效应。所报道的外消旋二肽的立体异构拆分非常有用。它可用于访问任何未知矩阵中各种立体异构化合物的数量。

更新日期：2019-11-18

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