Synthesis of N-Oxyamide-Linked Neoglycolipids

被引:12
作者
Chen, Na [1 ]
Xie, Juan [1 ]
机构
[1] PPSM, ENS Cachan, CNRS UMR 8531, F-94230 Cachan, France
关键词
MITSUNOBU REACTION; GLYCOLIPIDS; SPINACH; ACIDS; INHIBITORS; ANTITUMOR; ANALOGS;
D O I
10.1021/jo502128h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. beta-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.
引用
收藏
页码:10716 / 10721
页数:6
相关论文
共 36 条
[1]  
[Anonymous], ESSENTIALS GLYCOBIOL
[2]   The stimulating adventure of KRN 7000 [J].
Banchet-Cadeddu, Aline ;
Henon, Eric ;
Dauchez, Manuel ;
Renault, Jean-Hugues ;
Monneaux, Fanny ;
Haudrechy, Arnaud .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (09) :3080-3104
[3]   Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies [J].
Bartoszewicz, Agnieszka ;
Kalek, Marcin ;
Stawinski, Jacek .
TETRAHEDRON, 2008, 64 (37) :8843-8850
[4]   The mitsunobu reaction: Origin, mechanism, improvements, and applications [J].
But, Tracy Yuen Sze ;
Toy, Patrick H. .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) :1340-1355
[5]   β-Sugar Aminoxy Peptides As Rigid Secondary Structural Scaffolds [J].
Chandrasekhar, Srivari ;
Rao, Chennamaneni Lohitha ;
Reddy, Marepally Srinivasa ;
Sharma, Ganti Dattatreya ;
Kiran, Marelli Udaya ;
Naresh, Police ;
Chaitanya, Guturu Krishna ;
Bhanuprakash, Kotamarthi ;
Jagadeesh, Bharatam .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9443-9446
[6]   Extraordinary metabolic stability of peptides containing α-aminoxy acids [J].
Chen, Fei ;
Ma, Bin ;
Yang, Zong-Chang ;
Lin, Ge ;
Yang, Dan .
AMINO ACIDS, 2012, 43 (01) :499-503
[7]   Inhibitory effects of fatty acid monoesters of 2-O-β-D-glucosylglycerol on Epstein-Barr virus activation [J].
Colombo, D ;
Scala, A ;
Taino, IM ;
Toma, L ;
Ronchetti, F ;
Tokuda, H ;
Nishino, H ;
Nagatsu, A ;
Sakakibara, J .
CANCER LETTERS, 1998, 123 (01) :83-86
[8]   Synthesis of nucleoside aminooxy acids [J].
Gong, Yanchun ;
Peyrat, Sandrine ;
Sun, Hongbin ;
Xie, Juan .
TETRAHEDRON, 2011, 67 (37) :7114-7120
[9]   Synthesis of Oligosaccharide Mimetics with Glycoaminoxy Acids [J].
Gong, Yanchun ;
Sun, Hongbin ;
Xie, Juan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (34) :6027-6033
[10]   Synthesis of neoglycosphingolipid from methoxyamino-functionalized ceramide [J].
Ishida, Junya ;
Hinou, Hiroshi ;
Naruchi, Kentaro ;
Nishimura, Shin-Ichiro .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (04) :1197-1200