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Chemical Structure| 16469-68-4 Chemical Structure| 16469-68-4

Structure of 16469-68-4

Chemical Structure| 16469-68-4

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Product Citations

Product Citations

Gao, Feng ; Chang, Mengyang ; Meng, Xiang ; Xu, Hang ; Gnawali, Giri ; Dong, Yue , et al.

Abstract: Site-selective modification of biol. relevant secondary amines in peptides, proteins, and natural products has been challenging due to the similar reactivity between primary and secondary amines. Even for the secondary amines, their reactivities are significantly influenced by their structures and environment. Herein, we report a ynone Michael bioconjugation method for selective modification of secondary amines in unprotected peptides and proteins and complex natural products. We show that fine tuning the electronic effect of the ynones enables controlling the Michael acceptor reactivity for the selective reaction with the structurally different secondary amines in densely functionalized complex structures and complicated biol. environment.

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Product Details of [ 16469-68-4 ]

CAS No. :16469-68-4
Formula : C10H8O2
M.W : 160.17
SMILES Code : C#CC(C1=CC=C(OC)C=C1)=O
MDL No. :MFCD21262924

Safety of [ 16469-68-4 ]

Application In Synthesis of [ 16469-68-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 16469-68-4 ]

[ 16469-68-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 57508-48-2 ]
  • [ 16469-68-4 ]
  • [ 70959-86-3 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate; In ethanol; at 150℃; for 1.5h;Microwave irradiation; General procedure: an ethanolic solution of <strong>[57508-48-2]ethyl 3-amino-3-iminopropionate hydrochloride</strong> (6*HCl; 1equiv) was pretreated with Na2CO3 (1 equiv) for 10 min. After filtering, the ethynyl ketone (1.05 equiv) was added and the mixture in EtOH (3.5 mL) was irradiated at 150 C for 1.5 h (holdtime) in a pressure-rated glass tube (10 mL) using a CEM Discover microwave synthesizer by moderation of the initial magnetron power (200 W). After cooling in a flow of compressed air,the solution was immobilized on a Biotage ISOLUTE SCX-2column and eluted with EtOH-NH4OH (aq; 35%; 5:1) or ethanolic NH3 (2 M) to give the title compound.
 

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