环状和套索肽：序列测定、拓扑分析和轮烷形成。
Cyclic and Lasso Peptides: Sequence Determination, Topology Analysis, and Rotaxane Formation.
机构信息
Department of Chemistry and Biochemistry, Seton Hall University, South Orange, NJ, 07079, USA.
Department of Process Research and Development, Merck & Co., Inc., Rahway, NJ, 07065, USA.
出版信息
Angew Chem Int Ed Engl. 2018 May 22;57(21):6150-6154. doi: 10.1002/anie.201801299. Epub 2018 Apr 27.
Abstract
A broadly applicable chemical cleavage methodology to facilitate MS/MS sequencing was developed for macrocyclic and lasso peptides, which hold promise as exciting new therapeutics. Existing methods such as Edman degradation, CNBr cleavage, and enzymatic digestion are either limited in scope or completely fail in cleavage of constrained nonribosomal peptides. Importantly, the new method was utilized for synthesizing a unique peptide-based rotaxane (both cyclic and threaded) from the lasso peptide, benenodin-1 ΔC5.
摘要
开发了一种广泛适用于大环和套索肽的化学裂解方法，以促进 MS/MS 测序，这些肽类有望成为令人兴奋的新型治疗药物。现有的方法，如 Edman 降解、CNBr 裂解和酶消化，要么范围有限，要么完全无法裂解约束非核糖体肽。重要的是，新方法用于从套索肽 benenodin-1 ΔC5 中合成独特的基于肽的轮烷（环状和穿线）。
相似文献
1
Cyclic and Lasso Peptides: Sequence Determination, Topology Analysis, and Rotaxane Formation.环状和套索肽：序列测定、拓扑分析和轮烷形成。
Angew Chem Int Ed Engl. 2018 May 22;57(21):6150-6154. doi: 10.1002/anie.201801299. Epub 2018 Apr 27.
2
Lasso Peptide Benenodin-1 Is a Thermally Actuated [1]Rotaxane Switch.拉索肽 Benenodin-1 是一种热激活的 [1]轮烷开关。
J Am Chem Soc. 2017 Aug 2;139(30):10403-10409. doi: 10.1021/jacs.7b04830. Epub 2017 Jul 24.
3
Synthesis of All-Peptide-Based Rotaxane from a Proline-Containing Cyclic Peptide.基于脯氨酸的环肽的全肽轮烷的合成。
Biomacromolecules. 2024 Jun 10;25(6):3661-3670. doi: 10.1021/acs.biomac.4c00257. Epub 2024 May 29.
4
Ion mobility-mass spectrometry of lasso peptides: signature of a rotaxane topology.套索肽的离子淌度-质谱分析：轮烷拓扑结构的特征
Anal Chem. 2015 Jan 20;87(2):1166-72. doi: 10.1021/ac503772n. Epub 2014 Dec 31.
5
The Shuttling Cascade in Lasso Peptide Benenodin-1 is Controlled by Non-Covalent Interactions.拉索肽 Benenodin-1 中的穿梭级联由非共价相互作用控制。
Chemistry. 2022 Jan 24;28(5):e202103615. doi: 10.1002/chem.202103615. Epub 2021 Dec 2.
6
Synthesis of polyyne rotaxanes.轮烷型多炔的合成。
Org Lett. 2012 Jul 6;14(13):3424-6. doi: 10.1021/ol301392t. Epub 2012 Jun 18.
7
Synthesis of large [2]rotaxanes. The relationship between the size of the blocking group and the stability of the rotaxane.大环[2]轮烷的合成。封端基团的大小与轮烷稳定性的关系。
J Org Chem. 2013 Apr 19;78(8):3553-60. doi: 10.1021/jo302800t. Epub 2013 Apr 11.
8
A pH-sensitive lasso-based rotaxane molecular switch.一种基于 pH 敏感的套索轮烷分子开关。
Chemistry. 2013 Feb 25;19(9):2982-9. doi: 10.1002/chem.201203597. Epub 2013 Jan 23.
9
Sequence-specific peptide synthesis by an artificial small-molecule machine.人工小分子机器的序列特异性肽合成。
Science. 2013 Jan 11;339(6116):189-93. doi: 10.1126/science.1229753.
10
Reversible formation of a poly[3]rotaxane based on photo dimerization of an anthracene-capped [3]rotaxane.基于蒽封端[3]轮烷的光二聚作用可逆形成聚[3]轮烷。
Chem Commun (Camb). 2014 Nov 25;50(91):14105-8. doi: 10.1039/c4cc07044e.
引用本文的文献
1
Disulfide bridge-targeted metabolome mining unravels an antiparkinsonian peptide.二硫键靶向代谢组挖掘揭示了一种抗帕金森病肽。
Acta Pharm Sin B. 2024 Feb;14(2):881-892. doi: 10.1016/j.apsb.2023.09.006. Epub 2023 Sep 19.
2
Selective Conversion of Unactivated C-N Amide Bond to C-C bond via Steric and Electronic Resonance Destabilization.通过空间和电子共振去稳定化选择性地将未活化的 C-N 酰胺键转化为 C-C 键。
Org Lett. 2022 Sep 16;24(36):6525-6530. doi: 10.1021/acs.orglett.2c02420. Epub 2022 Sep 6.
3
How to harness biosynthetic gene clusters of lasso peptides.如何利用套索肽的生物合成基因簇。
J Ind Microbiol Biotechnol. 2020 Oct;47(9-10):703-714. doi: 10.1007/s10295-020-02292-6. Epub 2020 Jul 23.
4
Attempting to synthesize lasso peptides using high pressure.尝试使用高压合成套索肽。
PLoS One. 2020 Jun 24;15(6):e0234901. doi: 10.1371/journal.pone.0234901. eCollection 2020.
5
Amide Bond Activation of Biological Molecules.生物分子的酰胺键活化。
Molecules. 2018 Oct 12;23(10):2615. doi: 10.3390/molecules23102615.
本文引用的文献
1
Albusnodin: an acetylated lasso peptide from Streptomyces albus.白霉素：来自白色链霉菌的乙酰化套索肽。
Chem Commun (Camb). 2018 Feb 1;54(11):1339-1342. doi: 10.1039/c7cc08620b.
2
The Current State of Peptide Drug Discovery: Back to the Future?肽类药物发现的现状：回到未来？
J Med Chem. 2018 Feb 22;61(4):1382-1414. doi: 10.1021/acs.jmedchem.7b00318. Epub 2017 Aug 11.
3
Lasso Peptide Benenodin-1 Is a Thermally Actuated [1]Rotaxane Switch.拉索肽 Benenodin-1 是一种热激活的 [1]轮烷开关。
J Am Chem Soc. 2017 Aug 2;139(30):10403-10409. doi: 10.1021/jacs.7b04830. Epub 2017 Jul 24.
4
Structure of the Lasso Peptide Isopeptidase Identifies a Topology for Processing Threaded Substrates.拉索肽异肽酶的结构确定了一种处理穿线底物的拓扑结构。
J Am Chem Soc. 2016 Dec 21;138(50):16452-16458. doi: 10.1021/jacs.6b10389. Epub 2016 Dec 7.
5
Near-Quantitative Aqueous Synthesis of Rotaxanes via Bioconjugation to Oligopeptides and Proteins.通过生物偶联到寡肽和蛋白质来进行近乎定量的水相轮烷合成。
J Am Chem Soc. 2016 Nov 30;138(47):15307-15310. doi: 10.1021/jacs.6b10231. Epub 2016 Nov 17.
6
Sliding-Ring Catenanes.滑环轮烷。
J Am Chem Soc. 2016 Aug 17;138(32):10214-25. doi: 10.1021/jacs.6b04982. Epub 2016 Aug 4.
7
Site-selective chemical cleavage of peptide bonds.肽键的位点选择性化学裂解
Chem Commun (Camb). 2016 May 7;52(37):6304-7. doi: 10.1039/c6cc01509c. Epub 2016 Apr 18.
8
Lasso peptides: an intriguing class of bacterial natural products.套索肽：一类引人入胜的细菌天然产物。
Acc Chem Res. 2015 Jul 21;48(7):1909-19. doi: 10.1021/acs.accounts.5b00156. Epub 2015 Jun 16.
9
Development of Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to Applications.准轮烷和轮烷的发展：从合成到刺激响应运动再到应用
Chem Rev. 2015 Aug 12;115(15):7398-501. doi: 10.1021/cr5005869. Epub 2015 Mar 3.
10
Lessons in de novo peptide sequencing by tandem mass spectrometry.串联质谱法从头进行肽测序的经验教训。
Mass Spectrom Rev. 2015 Jan-Feb;34(1):43-63. doi: 10.1002/mas.21406.
Zotero 插件