• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

通往手性黑色素之路：左旋多巴氧化聚合过程中卟啉杂聚集体的动态“从印记到模板”超分子作用

En Route to a Chiral Melanin: The Dynamic "From-Imprinted-to-Template" Supramolecular Role of Porphyrin Hetero-Aggregates During the Oxidative Polymerization of L-DOPA.

作者信息

Gaeta Massimiliano, Randazzo Rosalba, Villari Valentina, Micali Norberto, Pezzella Alessandro, Purrello Roberto, d'Ischia Marco, D'Urso Alessandro

机构信息

Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Catania, Italy.

Consiglio Nazionale delle Ricerche-IPCF Istituto per i Processi Chimico-Fisici, Messina, Italy.

出版信息

Front Chem. 2020 Dec 21;8:616961. doi: 10.3389/fchem.2020.616961. eCollection 2020.

DOI:10.3389/fchem.2020.616961
PMID:33409269
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7779627/
Abstract

Chiral porphyrin hetero-aggregates, produced from meso-tetrakis(4-N-methylpyridyl) porphyrin HT4 and copper(II) meso-tetrakis(4-sulfonatophenyl)porphyrin CuTPPS by an imprinting effect in the presence of L-3,4-dihydroxyphenylalanine (L-DOPA), are shown herein to serve as templates for the generation of chiral structures during the oxidative conversion of the amino acid to melanin. This remarkable phenomenon is suggested to involve the initial role of L-DOPA and related chiral intermediates like dopachrome as templates for the production of chiral porphyrin aggregates. When the entire chiral pool from DOPA is lost, chiral porphyrin hetero-aggregate would elicit axially chiral oligomer formation from 5,6-dihydroxyindole intermediates in the later stages of melanin synthesis. These results, if corroborated by further studies, may open unprecedented perspectives for efficient strategies of asymmetric melanin synthesis with potential biological and technological applications.

摘要

在手性3,4-二羟基苯丙氨酸（L-DOPA）存在下，通过印迹效应由中位-四（4-N-甲基吡啶基）卟啉HT4和中位-四（4-磺基苯基）铜（II）卟啉CuTPPS生成的手性卟啉杂聚体，在此显示为在氨基酸氧化转化为黑色素过程中生成手性结构的模板。这一显著现象被认为涉及L-DOPA和相关手性中间体（如多巴色素）作为手性卟啉聚集体生成模板的初始作用。当来自多巴的整个手性库消失时，手性卟啉杂聚体将在黑色素合成后期从5,6-二羟基吲哚中间体引发轴向手性低聚物的形成。如果进一步的研究证实了这些结果，可能会为不对称黑色素合成的有效策略开辟前所未有的前景，并具有潜在的生物学和技术应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/5af516b55a2e/fchem-08-616961-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/95c6f6aceb70/fchem-08-616961-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/f5cbcda7d708/fchem-08-616961-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/a699edd5881b/fchem-08-616961-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/d9abb191e013/fchem-08-616961-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/5af516b55a2e/fchem-08-616961-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/95c6f6aceb70/fchem-08-616961-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/f5cbcda7d708/fchem-08-616961-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/a699edd5881b/fchem-08-616961-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/d9abb191e013/fchem-08-616961-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5454/7779627/5af516b55a2e/fchem-08-616961-g0005.jpg

相似文献

1
En Route to a Chiral Melanin: The Dynamic "From-Imprinted-to-Template" Supramolecular Role of Porphyrin Hetero-Aggregates During the Oxidative Polymerization of L-DOPA.通往手性黑色素之路：左旋多巴氧化聚合过程中卟啉杂聚集体的动态“从印记到模板”超分子作用
Front Chem. 2020 Dec 21;8:616961. doi: 10.3389/fchem.2020.616961. eCollection 2020.
2
Induction and memory of chirality in porphyrin hetero-aggregates: the role of the central metal ion.卟啉杂聚集体中手性的诱导与记忆：中心金属离子的作用
Bioorg Med Chem. 2005 Sep 1;13(17):5159-63. doi: 10.1016/j.bmc.2005.05.035.
3
Chiral Recognition of L- and D- Amino Acid by Porphyrin Supramolecular Aggregates.卟啉超分子聚集体对 L-和 D-氨基酸的手性识别。
Molecules. 2018 Dec 27;24(1):84. doi: 10.3390/molecules24010084.
4
Self-Assembled Chiral Film Based on Melanin Polymers.基于黑色素聚合物的自组装手性薄膜。
Chirality. 2024 Jun;36(6):e23695. doi: 10.1002/chir.23695.
5
Chiral memory: induction, amplification, and switching in porphyrin assemblies.手性记忆：卟啉组装体中的诱导、放大及转换
Chirality. 2008 Mar;20(3-4):411-9. doi: 10.1002/chir.20464.
6
Chiral induction, memory, and amplification in porphyrin homoaggregates based on electrostatic interactions.基于静电相互作用的卟啉同聚集体中的手性诱导、记忆和放大。
Chemphyschem. 2009 Apr 14;10(6):954-62. doi: 10.1002/cphc.200800810.
7
Free radicals in melanin-cationic porphyrin complexes in the dark and under light irradiation.黑暗及光照条件下黑色素 - 阳离子卟啉复合物中的自由基。
Pigment Cell Res. 1993 Jun;6(3):134-9. doi: 10.1111/j.1600-0749.1993.tb00592.x.
8
Supramolecular Chiral Aggregation of Porphyrin Induced by Photo-Generated Triphenylamines Radical Cations.光生三苯胺自由基阳离子诱导的卟啉超分子手性聚集
Small Methods. 2025 Jan;9(1):e2400538. doi: 10.1002/smtd.202400538. Epub 2024 Jul 10.
9
From achiral porphyrins to template-imprinted chiral aggregates and further. Self-replication of chiral memory from scratch.从非手性卟啉到模板印迹手性聚集体，再进一步。从头开始的手性记忆自我复制。
J Am Chem Soc. 2002 Feb 13;124(6):894-5. doi: 10.1021/ja017159b.
10
Optical absorption and fluorescence spectroscopy studies of ground state melanin-cationic porphyrins complexes.基态黑色素-阳离子卟啉复合物的光吸收和荧光光谱研究
Biophys Chem. 1992 Nov;45(1):79-89. doi: 10.1016/0301-4622(92)87025-e.

引用本文的文献

1
Structural disorder as a key to photoprotection in eumelanin multimers.结构紊乱是真黑素多聚体中光保护的关键。
Chem Sci. 2025 Jul 1. doi: 10.1039/d5sc00920k.
2
Porphyrins as Chiroptical Conformational Probes for Biomolecules.卟啉作为生物分子的手性光学构象探针
Molecules. 2025 Mar 28;30(7):1512. doi: 10.3390/molecules30071512.
3
Additive Manufacturing of Engineered Living Materials with Bio-augmented Mechanical Properties and Resistance to Degradation.具有生物增强力学性能和抗降解性的工程活材料的增材制造。

本文引用的文献

1
Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8).手性锌卟啉的超分子手性诱导作用由对映纯的半杯[烷]冠醚（n = 6,8）引起。
Chem Commun (Camb). 2019 Nov 28;55(96):14434-14437. doi: 10.1039/c9cc07150d.
2
Chiral Recognition of L- and D- Amino Acid by Porphyrin Supramolecular Aggregates.卟啉超分子聚集体对 L-和 D-氨基酸的手性识别。
Molecules. 2018 Dec 27;24(1):84. doi: 10.3390/molecules24010084.
3
Chirality Enhancement of Porphyrin Supramolecular Assembly Driven by a Template Preorganization Effect.
Adv Funct Mater. 2023 Jun 12;33(24). doi: 10.1002/adfm.202300332. Epub 2023 Mar 10.
模板预组织效应驱动的卟啉超分子组装的手性增强
Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10656-10660. doi: 10.1002/anie.201806192. Epub 2018 Jul 15.
4
The Late Stages of Melanogenesis: Exploring the Chemical Facets and the Application Opportunities.黑色素生成的晚期阶段：探索化学方面和应用机会。
Int J Mol Sci. 2018 Jun 13;19(6):1753. doi: 10.3390/ijms19061753.
5
Polydopamine Surface Chemistry: A Decade of Discovery.聚多巴胺表面化学：十年探索。
ACS Appl Mater Interfaces. 2018 Mar 7;10(9):7523-7540. doi: 10.1021/acsami.7b19865. Epub 2018 Feb 26.
6
A switchable self-assembling and disassembling chiral system based on a porphyrin-substituted phenylalanine-phenylalanine motif.基于卟啉取代苯丙氨酸-苯丙氨酸模体的可切换自组装和自拆卸手性体系。
Nat Commun. 2016 Sep 1;7:12657. doi: 10.1038/ncomms12657.
7
Controlled chiral supramolecular assemblies of water soluble achiral porphyrins induced by chiral counterions.手性抗衡离子诱导的水溶性非手性卟啉的可控手性超分子组装体
Chem Commun (Camb). 2016 Aug 11;52(67):10253-6. doi: 10.1039/c6cc04427a.
8
Chirality of self-assembled achiral porphyrins induced by chiral Zn(ii) Schiff-base complexes and maintained after spontaneous dissociation of the templates: a new case of chiral memory.手性锌（II）席夫碱配合物诱导自组装非手性卟啉的手性，并在模板自发解离后得以保持：手性记忆的新案例
Chem Commun (Camb). 2016 Jun 30;52(55):8518-21. doi: 10.1039/c6cc04018g.
9
Aggregates of a cationic porphyrin as supramolecular probes for biopolymers.作为生物聚合物超分子探针的阳离子卟啉聚集体。
J Inorg Biochem. 2015 Dec;153:361-366. doi: 10.1016/j.jinorgbio.2015.09.013. Epub 2015 Oct 9.
10
Hydrodynamic and Thermophoretic Effects on the Supramolecular Chirality of Pyrene-Derived Nanosheets.流体动力学和热泳对芘衍生纳米片超分子手性的影响。
Chemistry. 2015 Jun 22;21(26):9505-13. doi: 10.1002/chem.201500932. Epub 2015 May 26.