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Synthesis, Antioxidant Activity, and Structure–Activity Relationship of SCAP1 Analogues
International Journal of Peptide Research and Therapeutics ( IF 2.5 ) Pub Date : 2020-04-13 , DOI: 10.1007/s10989-020-10061-3
Rani Maharani , Ace Tatang Hidayat , Irana Rahmawati Sabana , Anastasya Firdausi , Alifah Aqmarina , Dessy Yulyani Kurnia , Mufti Hanif Amrullah , Achmad Zainuddin , Desi Harneti , Nurlelasari , Unang Supratman

Nine analogues of antioxidant peptide SCAP1 were successfully synthesised using a solid-phase method on a 2-chlorotrytil resin. The compounds were obtained in a range of yields of 7.0–57.8%. The occurrence of aggregation during the synthesis is suspected to be responsible for the poor yields. All peptides were characterized by high-resolution time-of-flight mass spectrometry (HR-TOFMS) and nuclear magnetic resonance (NMR). The antioxidant activities of the SCAP1 analogues as well as SCAP1 were analysed utilising the 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) assay. The results revealed that all of the analysed peptides exhibited moderate antioxidant properties. Moreover, the evaluation of the structure–activity relationship showed that the Asn residue is an important requirement for the antioxidant activity of SCAP1. The replacement of Asn with other amino acid residues (Thr, Pro, Tyr, Trp and Phe) resulted in a decrease in the IC50 values of the peptides. Notably, however, the replacement of the Lys residue with Val marginally increased the activity.



中文翻译:

SCAP1类似物的合成,抗氧化活性和结构-活性关系

抗氧化剂肽SCAP1的九个类似物已成功地使用固相方法在2-chlorotrytil树脂上合成。这些化合物的收率范围为7.0–57.8%。怀疑在合成过程中发生聚集是造成产量低的原因。所有肽均通过高分辨率飞行时间质谱(HR-TOFMS)和核磁共振(NMR)进行了表征。SCAP1类似物以及SCAP1的抗氧化活性是通过2,2-二苯基-1-picryl-肼基水合物(DPPH)分析进行分析的。结果表明,所有分析的肽均表现出中等的抗氧化性能。此外,对构效关系的评估表明,Asn残基是SCAP1抗氧化活性的重要要求。肽的50个值。然而,值得注意的是,用Val置换Lys残基稍微增加了活性。

更新日期:2020-04-13
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