Efficient total synthesis of pentosidine, an advanced glycation endproduct

被引:18
作者
Sugiyama, H
Yokokawa, F
Shioiri, T [1 ]
Katagiri, N
Oda, O
Ogawa, H
机构
[1] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
[2] Biodynam Res Inst, Mizuho Ku, Nagoya, Aichi 4678633, Japan
[3] Shinseikai Dai Ichi Hosp, Mizuho Ku, Nagoya, Aichi 4678633, Japan
关键词
pentosidine; an advanced glycation endproduct; asymmetric synthesis; cyclization; amino acids and derivatives;
D O I
10.1016/S0040-4039(99)00204-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient total synthesis of pentosidine (1), an advanced glycation endproduct, was achieved using the asymmetric alkylation of a chiral schiff base (2), the intramolecular guanylation with mercury (II) chloride, and the quaternization accompanied by removal of the trityl group as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2569 / 2572
页数:4
相关论文
共 13 条
[1]   INCREASED COLLAGEN-LINKED PENTOSIDINE LEVELS AND ADVANCED GLYCOSYLATION END-PRODUCTS IN EARLY DIABETIC NEPHROPATHY [J].
BEISSWENGER, PJ ;
MOORE, LL ;
BRINCKJOHNSEN, T ;
CURPHEY, TJ .
JOURNAL OF CLINICAL INVESTIGATION, 1993, 92 (01) :212-217
[2]  
FRIEDLANDER MA, 1995, AM J KIDNEY DIS, V25, P441
[3]   EFFECTS OF KIDNEY OR KIDNEY-PANCREAS TRANSPLANTATION ON PLASMA PENTOSIDINE [J].
HRICIK, DE ;
SCHULAK, JA ;
SELL, DR ;
FOGARTY, JF ;
MONNIER, VM .
KIDNEY INTERNATIONAL, 1993, 43 (02) :398-403
[4]   IMPROVED METHOD FOR THE PREPARATION OF GUANIDINES [J].
KIM, KS ;
QIAN, LG .
TETRAHEDRON LETTERS, 1993, 34 (48) :7677-7680
[5]   An improved procedure for the preparation of isothiocyanates from primary amines by using hydrogen peroxide as the dehydrosulfurization reagent [J].
Li, G ;
Tajima, H ;
Ohtani, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4539-4540
[6]  
MATHIAS LJ, 1979, SYNTHESIS-STUTTGART, P561
[7]   MAILLARD REACTION-PRODUCTS AND THEIR RELATION TO COMPLICATIONS IN INSULIN-DEPENDENT DIABETES-MELLITUS [J].
MCCANCE, DR ;
DYER, DG ;
DUNN, JA ;
BAILIE, KE ;
THORPE, SR ;
BAYNES, JW ;
LYONS, TJ .
JOURNAL OF CLINICAL INVESTIGATION, 1993, 91 (06) :2470-2478
[8]  
OGURI T, 1978, CHEM PHARM BULL, V26, P803
[9]  
PLIEV TN, 1973, KHIM GETEROTSIKL+, P1686
[10]  
SELL DR, 1989, J BIOL CHEM, V264, P21597