Synthesis of novel and non-natural ceramide analogues derived from L-glutamic acid

被引:15
作者
Shikata, K [1 ]
Azuma, H [1 ]
Tachibana, T [1 ]
Ogino, K [1 ]
机构
[1] Osaka City Univ, Grad Sch Engn, Dept Bioappl Chem, Sumiyoshi Ku, Osaka 5588585, Japan
关键词
ceramide; glutamic acid; sphingolipids;
D O I
10.1016/S0040-4020(02)00558-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel and non-natural ceramide analogues, having a different methylene spacer between the primary hydroxymethyl group and aminomethane of sphingosine backbone, have been prepared from L-glutamic acid. The key step in the preparation is the diastereoselective reduction of an enone adjacent to a Boc protected amino group by reducing agents. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5803 / 5809
页数:7
相关论文
共 27 条
[1]  
Ariga T, 1998, J LIPID RES, V39, P1
[2]   Stereospecific total syntheses of sphingosine and its analogues from L-serine [J].
Azuma, H ;
Tamagaki, S ;
Ogino, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3538-3541
[3]   Lipase-catalyzed enantiomeric resolution of ceramides [J].
Bakke, M ;
Takizawa, M ;
Sugai, T ;
Ohta, H .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6929-6938
[4]   The synthesis and biological characterization of a ceramide library [J].
Chang, YT ;
Choi, J ;
Ding, S ;
Prieschl, EE ;
Baumruker, T ;
Lee, JM ;
Chung, SK ;
Schultz, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1856-1857
[5]   Synthesis of ceramide analogues having the C(4)-C(5) bond of the long-chain base as part of an aromatic or heteroaromatic system [J].
Chun, J ;
He, LL ;
Byun, HS ;
Bittman, R .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7634-7640
[6]   Stereoselective synthesis of β-amino alcohols:: practical preparation of all four stereomers of N-PMB-protected sphingosine from L- and D-serine [J].
Chung, SK ;
Lee, JM .
TETRAHEDRON-ASYMMETRY, 1999, 10 (08) :1441-1444
[7]   Convenient synthesis of L-proline benzyl ester [J].
Córdova, A ;
Reed, NN ;
Ashley, JA ;
Janda, KD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (21) :3119-3122
[8]   Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate [J].
Cuvillier, O ;
Pirianov, G ;
Kleuser, B ;
Vanek, PG ;
Coso, OA ;
Gutkind, JS ;
Spiegel, S .
NATURE, 1996, 381 (6585) :800-803
[10]   STEREODIVERGENT SYNTHESES OF THREO-6-AMINO-6-DEOXYHEPTOSULOSE AND ERYTHRO-6-AMINO-6-DEOXYHEPTOSULOSE DERIVATIVES VIA AN OPTICALLY-ACTIVE OXAZOLIDINE ALDEHYDE [J].
GARNER, P ;
RAMAKANTH, S .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2609-2612