Stereoselective total synthesis of serine palmitoyl-CoA transferase inhibitors

被引：25

作者：

Byun, Hoe-Sup ^{[1
]}

Lu, Xuequan ^{[1
]}

Bittman, Robert ^{[1
]}

机构：

[1] CUNY Queens Coll, Dept Chem & Biochem, Flushing, NY 11367 USA

来源：

SYNTHESIS-STUTTGART | 2006年 / 15期

关键词：

sphingolipids; natural products; inhibitors; antifungal agents; stereoselective synthesis;

D O I：

10.1055/s-2006-942475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review summarizes the total syntheses of the fungal metabolites mycestericin, myriocin, viridiofungin, sulfamisterin, and sphingofungin. The syntheses are organized into three sections: the preparation of (a) the long chain and (b) the polar head group, and (c) the coupling of the two parts of the molecule. The mechanism of action of these potent inhibitors of serine palmitoyl-CoA transferase, the rate-limiting enzyme in the biosynthesis of sphingolipids, is also briefly described.

引用

页码：2447 / 2474

页数：28

共 85 条

[1] ALKYNE ISOMERIZATION REAGENTS - MIXED ALKALI-METAL AMIDES [J].

ABRAMS, SR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1333-1334

[2]

ALNEIRABEYEH M, 1976, SYNTHESIS-STUTTGART, P811

[3]

[Anonymous], 1994, Org. React

[4] TOTAL SYNTHESIS OF (+)-THERMOZYMOCIDIN (MYRIOCIN) FROM D-FRUCTOSE [J].

BANFI, L ;

BERETTA, MG ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (09) :488-490

[5] 2-BENZOYLAMINO-2-DEOXY-2-HYDROXYMETHYL-D-HEXONO-1,4-LACTONES - SYNTHESIS FROM D-FRUCTOSE AND UTILIZATION IN THE TOTAL SYNTHESIS OF THERMOZYMOCIDIN (MYRIOCIN) [J].

BANFI, L ;

BERETTA, MG ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1613-1619

[6] Organoselenium-based entry into versatile, α-(2-tributylstannyl)vinyl amino acids in scalemic form:: A new route to vinyl stannanes [J].

Berkowitz, DB ;

McFadden, JM ;

Chisowa, E ;

Semerad, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11031-11032

[7] Biology and chemistry of sphingosine-related metabolites [J].

Brunner, M ;

Koskinen, AMP .

CURRENT ORGANIC CHEMISTRY, 2004, 8 (17) :1629-1645

[8] Using genomic and lipidomic strategies to investigate sphingolipid function in the yeast heat-stress response [J].

Cowart, LA ;

Hannun, YA .

BIOCHEMICAL SOCIETY TRANSACTIONS, 2005, 33 :1166-1169

[9] REACTION OF ACETYL HYPOFLUORITE WITH PYRANOID AND FURANOID GLYCALS [J].

DAX, K ;

GLANZER, BI ;

SCHULZ, G ;

VYPLEL, H .

CARBOHYDRATE RESEARCH, 1987, 162 (01) :13-22

[10] SYNTHESIS OF ALPHA-AZIDO ALDEHYDES - STEREOSELECTIVE FORMAL ACCESS TO THE IMMUNOSUPPRESSANT MYRIOCIN [J].

DELOISY, S ;

THANG, TT ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1994, 35 (27) :4783-4786

← 1 2 3 4 5 6 7 8 9 →