Synthesis of biopterin and related pterin glycosides

被引：9
|
作者：
Hanaya, Tadashi [1 ]
Yamamoto, Hiroshi [2 ]
机构：
[1] Okayama Univ, Fac Sci, Dept Chem, Kita Ku, Okayama 7008530, Japan
[2] Shujitsu Univ, Sch Pharm, Naka Ku, Okayama 7038516, Japan
来源：
IUBMB LIFE | 2013年 / 65卷 / 04期
关键词：
pteridine; pterin glycoside; biopterin; ciliapterin; neopterin; limipterin; tepidopterin; asperopterin-A; protecting group; glycosylation; BACTERIUM CHLOROBIUM-LIMICOLA; SYNECHOCOCCUS SP PCC-7942; 1ST SYNTHESIS; EFFICIENT SYNTHESIS; ALPHA-GLUCOSIDE; ASPEROPTERIN-B; NITRIC-OXIDE; PTERIDINES; COFACTOR; ACID;
D O I：
10.1002/iub.1137
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Certain pterins having a hydroxyalkyl side chain at C-6 have been found as glycosidic forms in certain prokaryotes, such as 2-O-(-D-glucopyranosyl)biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium. Synthetic studies on glycosides of biopterin and related pterins have been made in view of the structural proof as well as for closer examination of their biological activities and functions. The syntheses of these natural pterin glycosides have effectively been achieved, mostly through appropriately protected N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors, and are reviewed here. (c) 2013 IUBMB Life 65(4):300309, 2013.
引用
收藏
页码：300 / 309
页数：10
相关论文
共 50 条
  • [41] Recent advances on synthesis of C-glycosides
    Parida, Sonali Priyadarshini
    Das, Tapaswini
    Ahemad, Mohammed Ansar
    Pati, Tapaswini
    Mohapatra, Seetaram
    Nayak, Sabita
    CARBOHYDRATE RESEARCH, 2023, 530
  • [42] Attenuation of Biopterin Synthesis Prevents Escherichia coli K1 Invasion of Brain Endothelial Cells and the Development of Meningitis in Newborn Mice
    Shanmuganathan, Muthusamy V.
    Krishnan, Subramanian
    Fu, Xiaowei
    Prasadarao, Nemani V.
    JOURNAL OF INFECTIOUS DISEASES, 2013, 207 (01): : 61 - 71
  • [43] Diversity-Oriented Synthesis of Steviol Glycosides
    Qiao, Zhi
    Liu, Hui
    Sui, Jing-Jing
    Liao, Jin-Xi
    Tu, Yuan-Hong
    Schmidt, Richard R.
    Sun, Jian-Song
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19): : 11480 - 11492
  • [44] Synthesis of hetaryl glycosides and their glycosyl donor properties
    Huchel, U
    Schmidt, C
    Schmidt, RR
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (07) : 1353 - 1360
  • [45] Synthesis and antitumor activity of a group ofdiosgenyl glycosides
    Shu Jie Hou
    Chinese Chemical Letters, 2007, (07) : 769 - 772
  • [46] Isoflavone glycosides:: Synthesis and evaluation as α-glucosidase inhibitors
    Wei, Guo
    Yu, Biao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (18) : 3156 - 3163
  • [47] SYNTHESIS OF QUERCETIN GLYCOSIDES AND THEIR α-GLUCOSIDASE INHIBITORY ACTIVITIES
    Xu, Bixue
    Liang, Guangyi
    Wen, Zhonghang
    Hu, Zhanxin
    Yuan, Jie
    Chen, Hongju
    Zhang, Limei
    HETEROCYCLES, 2016, 92 (07) : 1245 - 1260
  • [48] Synthesis and antitumor activity of a group of diosgenyl glycosides
    Hou, Shu Jie
    Zou, Chuan Chun
    Zhou, Liang
    Xu, Peng
    Yu, De Quan
    Lei, Ping Sheng
    CHINESE CHEMICAL LETTERS, 2007, 18 (07) : 769 - 772
  • [49] Synthesis of Capsaicin Glycosides and 8-Nordihydrocapsaicin Glycosides as Potential Weight-Loss Formulations
    Katsuragi, Hisashi
    Shimoda, Kei
    Kimura, Eriko
    Hamada, Hiroki
    BIOCHEMISTRY INSIGHTS, 2010, 3 : 34 - 38
  • [50] Advances in the Synthesis of C-Glycosides from Glycals
    Guo, Zhenyan
    Bai, Jinhe
    Liu, Miao
    Xiong, Decai
    Ye, Xinshan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (10) : 3094 - 3111
12345