期刊文献+

13^2-羟基脱镁叶绿酸-a甲酯的合成及其立体结构的表征与确定 被引量:5

Synthesis of Methyl 13^2-Hydroxylpheophorbide-a and Characterization and Identification of Their Stereostructure
下载PDF
导出
摘要 以叶绿素-a为起始原料,经过酯交换和去除金属离子得到焦脱镁叶绿酸-a甲酯,在热乙酸中的空气氧化得到132(R/S)-132-羟基脱镁叶绿酸-a甲酯的混合物,在氢氧化钾甲醇溶液中的空气氧化主要给出作为氧化和重排产物的红紫素-18甲酯.通过层析将非对映体相互分离,对其核磁共振氢谱进行讨论并对立体结构进行表征和确定. Chlorophyll-a is used as starting material and comnverted into methyl pyropheophorbide-a by transesterification and removement of metal ion.13^2(R/S)-132-hydroxylpheophorbide-a as a mixture is obtained by allomerization in heat acetic acid.The purpurin-18 methyl ester as a major oxidized and rearranged product is produced by air-oxidation in methanolic potassium hydroxide.The diastereoisomers are separated by column chromatography and stereostructures are characterized and identified by 1H NMR spectra.
出处 《烟台大学学报(自然科学与工程版)》 CAS 北大核心 2011年第1期27-33,共7页 Journal of Yantai University(Natural Science and Engineering Edition)
基金 山东省自然科学基金资助项目(Y2008B49)
关键词 叶绿素-A 二氢卟吩 脱镁叶绿酸-a甲酯 立体化学 表征 chlorophyll-a chlorin methyl pheophorbidel-a stereochemistry characterization
  • 相关文献

参考文献8

二级参考文献21

  • 1韩光范,王进军,常秀娟.红紫素-18酰亚胺衍生物的合成及其可见光谱的研究[J].有机化学,2004,24(2):187-194. 被引量:13
  • 2王树军,阮文娟,朱志昂.卟啉组装体的结构、功能和性质[J].化学通报,2005,68(3):161-166. 被引量:8
  • 3王进军.叶绿素-a衍生物的化学反应和多取代卟吩(啉)合成的研究进展[J].有机化学,2005,25(11):1353-1371. 被引量:57
  • 4荆济荣,李家柱,王进军.叶绿素-a衍生物卟吩环上取代基的变化对其可见光谱的影响[J].烟台大学学报(自然科学与工程版),2007,20(2):102-107. 被引量:3
  • 5Tamikaki H. Supramolecular structure in extramembranous antennae of green photosynthetic bacteria [ J ]. Cood Chem Rev, 1996, 148:183-197.
  • 6Yagai S, Miyatake T, Tamiaki H. Self-assembly of synthetic 81-hydroxy-chlorophyll analogues [ J]. J Photochem Photobiol B: Biol, 1999, 52: 74-85.
  • 7Saga Y, Miyatake T, Tamiaki H. Self-assemble of synthetic zinc chlorine in a silicate micelle prepared by sol- gel process [ J]. Bioorg Med Chem Left, 2002, 12:1229- 1231.
  • 8Yagai S, Miyatakake T, Shimono Y. Supramolecular structure of self-assembled synthetic zinc 13^1-oxo-chlorins possessing a primary, secondary or tertiary alcoholic 3^1-hydroxyl group: visible spectroscopic and molecular modeling studies [ J]. Photochem Photobiol, 2001,73 (2) :153-163.
  • 9SmithKM, Bisset GM F, Bushell M J. Partial synthesis of optically pure methyl bacteriophophorbides a and d from methyl pheophorbide a [J]. J Org Chem, 1980, 45: 2218-2224.
  • 10Tamiaki H, Kouraba M. Synthesis of chlorophyll a homologs by wittig and knoevenagel reactions with methyl pyropheophorbide-d [J]. Tetrahedron, 1997, 53 (31) : 10677 -10689.

共引文献59

同被引文献35

  • 1王进军.叶绿素-a衍生物的化学反应和多取代卟吩(啉)合成的研究进展[J].有机化学,2005,25(11):1353-1371. 被引量:57
  • 2李家柱.具有叶绿素碳架的光动力抗癌药物的合成研究[D].烟台:烟台大学,2008.
  • 3Chen Yihui, Lin Guolin, Pendey, R. K. Synthesis of bacteriochlorind and their potential untility in photodynamic [ J ].Current Org Chem, 2004, 8: 1105-1134.
  • 4Smith K M, Bissert G M F, Bushell M J. Partial synthe- sis of optically pure methyl bacateriophophorbide a and d from methyl pheophorbide a [ J] , J Org Chem, 1980, 45 : 2218- 2224.
  • 5Bruckner C, Mccarthy J R, Daniell H W, et al. A spectroscopic and computational study of the singlet and triplet excited states of synthetic β-functionalized chlorins [ J ]. Chemi- cal Physics, 2003,294: 285-303.
  • 6Kunieda M, Mizoguchi T, Tamiaki H. Syntheses and optical properities of stable 8-alkylidene-bacterio-chlorins mimic- king the molecular structures of natural bacteriochlorophylls-b and g[ J ]. Tetrahedron, 2004, 60 : 11349-11357.
  • 7Chen Yihui, Lin Guolin, Pendey R K. Synthesis of bac- teriochlorind and their potential nntility in photodynamic J ]. Current Org Chem, 2004, 8: 1105-1134.
  • 8Goswami L N, Ethiraian M, Dobhal M P, et al. Remark- able features of McMurry reaction condition in dimerization of formyl-and 2-formylvinylpurpurinmides[Jl. J Org Chem, 2009, 74 ( 2 ), 568-579.
  • 9Wang Jinjun, Li Jiazhu, Li Yunwei, et al. Synthesis of isoxazoline-linked chlorins and their in vitro cell viabilities [ J ]. J Porphyrins Phthalocyanines, 2010, 14:859-865.
  • 10Pandey R K, Goswami L N, Chen Y H, et al. Nature: a rich source for developing multifunctional agents, tumor-imaging and photodynamic therapy[ J]. Laser Surg Med, 2006, 38,445 --467.

引证文献5

二级引证文献2

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部