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The Dominant Role of Oxygen in Modulating the Chemical Evolution Pathways of Tyrosine in Peptides: Dityrosine or Melanin
Rai, Xiaokang1,2; Zou, Qianli1; Yuan, Chengqian1; Chang, Rui1,2; Xing, Ruirui1; Yan, Xuehai1,2,3
2019-04-23
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
Volume58Issue:18Pages:5872-5876
AbstractIn diverse biological systems, the oxidation of tyrosine to melanin or dityrosine is crucial for the formation of crosslinked proteins and thus for the realization of their structural, biological, and photoactive functionalities; however, the predominant factor in determining the pathways of this chemical evolution has not been revealed. Herein, we demonstrate for tyrosine-containing amino acid derivatives, peptides, and proteins that the selective oxidation of tyrosine to produce melanin or dityrosine can be readily realized by manipulating the oxygen concentration in the reaction system. This oxygen-dependent pathway selection reflects the selective chemical evolution of tyrosine to dityrosine and melanin in anaerobic and aerobic microorganisms, respectively. The resulting melanin- and dityrosine-containing nanomaterials reproduce key functions of their natural counterparts with respect to their photothermal and photoluminescent characteristics, respectively. This work reveals the plausible role of oxygen in the chemical evolution of tyrosine derivatives and provides a versatile strategy for the rational design of tyrosine-based multifunctional biomaterials.
Keywordchemical evolution peptides peptide materials self-assembly tyrosine oxidation
DOI10.1002/anie.201814575
Language英语
WOS KeywordCROSS-LINKING ; CRYSTAL
Funding ProjectNational Natural Science Foundation of China[21522307] ; National Natural Science Foundation of China[21773248] ; National Natural Science Foundation of China[21802144] ; National Natural Science Foundation of China[21802143] ; National Natural Science Fund BRICS STI Framework Programme[51861145304] ; Innovation Research Community Science Fund[21821005] ; Key Research Program of Frontier Sciences of the Chinese Academy of Sciences (CAS)[QYZDB-SSW-JSC034]
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Fund BRICS STI Framework Programme ; Innovation Research Community Science Fund ; Key Research Program of Frontier Sciences of the Chinese Academy of Sciences (CAS)
WOS IDWOS:000465413400008
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/28230
Collection中国科学院过程工程研究所
Corresponding AuthorYan, Xuehai
Affiliation1.Chinese Acad Sci, Inst Proc Engn, State Key Lab Biochem Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Inst Proc Engn, Ctr Mesosci, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Rai, Xiaokang,Zou, Qianli,Yuan, Chengqian,et al. The Dominant Role of Oxygen in Modulating the Chemical Evolution Pathways of Tyrosine in Peptides: Dityrosine or Melanin[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(18):5872-5876.
APA Rai, Xiaokang,Zou, Qianli,Yuan, Chengqian,Chang, Rui,Xing, Ruirui,&Yan, Xuehai.(2019).The Dominant Role of Oxygen in Modulating the Chemical Evolution Pathways of Tyrosine in Peptides: Dityrosine or Melanin.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(18),5872-5876.
MLA Rai, Xiaokang,et al."The Dominant Role of Oxygen in Modulating the Chemical Evolution Pathways of Tyrosine in Peptides: Dityrosine or Melanin".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.18(2019):5872-5876.
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