Citation: Jiang Qiyong, Zhang Zhu, Liu Yang, Yao Nannan, Wang Jinjun. Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1814-1823. doi: 10.6023/cjoc201610045 shu

Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein

Jiang Qiyong ^a ,
Zhang Zhu ^b ,
Liu Yang ^b ,
Yao Nannan ^b ,
Wang Jinjun ^a,b,,

a.
Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005
b.
College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Corresponding author: Wang Jinjun, wjj1955@163.com
Received Date: 31 October 2016
Revised Date: 16 January 2017
Available Online: 1 July 2017
Fund Project: the National Natural Science Foundations of China 21272048the University Science and Technology Plan Projects of Shandong Province J15LC51Project supported by the National Natural Science Foundations of China (No. 21272048) and the University Science and Technology Plan Projects of Shandong Province (No. J15LC51)

Figures(5)

Pyropheophorbide-a (b) methyl esters were used as starting materials to form different chlorophyll degradation products by the modification of the exocyclic ring and the metallization of the chromophore. The new functional groups were introduced at 20-position via the Vilsmeier acylation and the Blanc hydroxymethylation. The active structures of chlorin peripheries were oxidized using osmium tetroxide, thaillum nitrate and air as oxidizing agent to introduce the formyl group and the formylmethyl group at 3-, 7-or 12-postion and on the exocyclic ring, respectively. A series of unreported chlorin aldehydes related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra. The reaction mechanisms on the hydroformylation for the chlorophyllous chlorins were discussed and the interactions of new compounds with bovine serum albumins were researched.
- chlorophyll,
- chlorin,
- bovine serum albumins,
- chemical modification,
- florescence quenching
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