Synthesis of oligomers derived from amide-linked neuraminic acid analogues

被引：44

作者：

Gregar, TQ

Gervay-Hague, J

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 04期

关键词：

D O I：

10.1021/jo035312+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Fluoren-9-ylmethoxycarbonyl-protected sugar amino acids derived from alpha-O-methoxy- and 2,3-dehydroneuraminic acids have been prepared. Incorporation of these monomer units into solid-phase synthesis led to the efficient synthesis of two series of oligomers varying from one to eight units in length. The (1-->5)-linked amides of 2,3-dehydroneuraminic acid were further subjected to hydrogenation giving a third series of oligomers with a beta-hydrido substituent at the anomeric carbon.

引用

收藏

页码：1001 / 1009

页数：9

相关论文

共 39 条

[1] Helix formation and folding in γ-peptides and their vinylogues [J].

Baldauf, C ;

Günther, R ;

Hofmann, HJ .

HELVETICA CHIMICA ACTA, 2003, 86 (07) :2573-2588

[2] SYNTHESIS OF 4-EPI-2-DEOXY-2-H-EQ-N-ACETYLNEURAMINIC ACID AND 2,4-DIDEOXY-2-H-EQ-N-ACETYLNEURAMINIC ACID [J].

BANDGAR, BP ;

ZBIRAL, E .

CARBOHYDRATE RESEARCH, 1995, 270 (02) :201-210

[3] HELICAL EPITOPE OF THE GROUP-B MENINGOCOCCAL ALPHA(2-8)-LINKED SIALIC-ACID POLYSACCHARIDE [J].

BRISSON, JR ;

BAUMANN, H ;

IMBERTY, A ;

PEREZ, S ;

JENNINGS, HJ .

BIOCHEMISTRY, 1992, 31 (21) :4996-5004

[4] Cyclic homooligomers of furanoid sugar amino acids [J].

Chakraborty, TK ;

Srinivasu, P ;

Bikshapathy, E ;

Nagaraj, R ;

Vairamani, M ;

Kumar, SK ;

Kunwar, AC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6257-6263

[5]

Chakraborty TK, 2002, COMB CHEM HIGH T SCR, V5, P373

[6] Sugar amino acids and their uses in designing bioactive molecules [J].

Chakraborty, TK ;

Ghosh, S ;

Jayaprakash, S .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (04) :421-435

[7] Furanoid sugar amino acid based peptidomimetics: well-defined solution conformations to gel-like structures [J].

Chakraborty, TK ;

Jayaprakash, S ;

Srinivasu, P ;

Madhavendra, SS ;

Sankar, AR ;

Kunwar, AC .

TETRAHEDRON, 2002, 58 (14) :2853-2859

[8] Models of higher-order structure: foldamers and beyond [J].

Cubberley, MS ;

Iverson, BL .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2001, 5 (06) :650-653

[9] Automated solid-phase synthesis and structural investigation of β-peptidosulfonamides and β-peptidosulfonamide/β-peptide hybrids:: β-peptidosulfonamide and β-peptide foldamers are two of a different kind [J].

de Jong, R ;

Rijkers, DTS ;

Liskamp, RMJ .

HELVETICA CHIMICA ACTA, 2002, 85 (12) :4230-4243

[10] Solid state and solution conformation of 2-pyridinecarboxylic acid hydrazides:: a new structural motif for foldamers [J].

Garric, J ;

Léger, JM ;

Grelard, A ;

Ohkita, M ;

Huc, I .

TETRAHEDRON LETTERS, 2003, 44 (07) :1421-1424

← 1 2 3 4 →