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首页> 外文期刊>International Journal of Peptide Research and Therapeutics >To Rink or Not to Rink Amide Link, that is the Question to Address for More Economical and Environmentally Sound Solid-Phase Peptide Synthesis
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To Rink or Not to Rink Amide Link, that is the Question to Address for More Economical and Environmentally Sound Solid-Phase Peptide Synthesis

机译：溜进或不溜进酰胺键，这是解决更经济和对环境无害的固相肽合成所要解决的问题

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摘要

A comparative study is presented on the solid-phase peptide synthesis (SPPS) of the acyl carrier protein (ACP 65–74) sequence on a series of Rink amide resins possessing different matrix structures: poly(vinyl alcohol)-graft-poly(ethylene glycol) (PVA-g-PEG, 4), Tentagel-S-RAM (TG, 5), NovaGel (NG, 6), ChemMatrix (CM, 7) and polystyrene-divinylbenzene (PS-DVB, 8). In this comparison, the PEG-containing resins proved significantly better suited for the synthesis of pure ACP target sequence than the conventional PS-DVB solid supports (75–90% versus 52% crude purity). Amongst themselves, the PEG resins 4-7 exhibited similar capacity for providing pure peptide. Selecting PVA-g-PEG resin for a comparison of Rink amide linker versus no linker, the ACP (65–74) sequence was synthesized directly on the PVA-g-PEG resin 1, under identical conditions as employed in the synthesis on resin 4 bearing the Fmoc Rink linker, except for the final cleavage step, which was performed under more environmentally sound conditions using ester displacement with aqueous ammonia. Relative to its Rink amide counterpart 4, PVA-g-PEG resin 1 was cheaper to produce and possessed twice as much loading capacity (0.48 vs. 0.81 mmol/g). Moreover, Rink-less resin 1 gave higher yields of isolated pure peptide (61 vs. 45%) relative to its Fmoc Rink linker counterpart 4. In light of these results, the importance of the linker has been brought into question. As the need for large scale solid-phase peptide synthesis grows with greater demand for peptide products, ideal resins should be inexpensive to produce and employable under environmentally sound conditions to provide pure products. In this light, PVA-g-PEG resin 1 has demonstrated significant promise for economic and “green” SPPS.
机译：在一系列具有不同基质结构的Rink酰胺树脂上，对酰基载体蛋白（ACP 65–74）序列的固相肽合成（SPPS）进行了比较研究：聚乙烯醇-接枝-聚乙烯乙二醇）（PVA-g-PEG，4），Tentagel-S-RAM（TG，5），NovaGel（NG，6），ChemMatrix（CM，7）和聚苯乙烯-二乙烯基苯（PS-DVB，8）。在此比较中，与传统的PS-DVB固体支持物相比，含PEG的树脂被证明明显更适合于纯ACP目标序列的合成（75-90％对52％的粗纯度）。在它们之中，PEG树脂4-7表现出相似的提供纯肽的能力。选择PVA-g-PEG树脂以比较Rink酰胺接头与无接头，ACP（65-74）序列直接在PVA-g-PEG树脂1上合成，条件与在树脂4上合成所使用的条件相同除了最后的裂解步骤外，该方法带有Fmoc Rink接头，该步骤在更环保的条件下使用氨水置换酯进行。相对于Rink酰胺对应物4，PVA-g-PEG树脂1的生产成本更低，并且具有两倍的负载量（0.48对0.81 mmol / g）。此外，相对于其Fmoc Rink接头对应物4，无Rink树脂1产生的分离出的纯肽产率更高（61对45％）。鉴于这些结果，对接头的重要性提出了质疑。随着对大规模固相肽合成的需求随着对肽产物的更大需求而增长，理想的树脂应廉价生产并且可在无害环境的条件下用于提供纯产物。有鉴于此，PVA-g-PEG树脂1已显示出经济和“绿色” SPPS的巨大前景。

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