Synthesis of a N-acylsulfamide linked dinucleoside and its incorporation into an oligonucleotide

被引：11

作者：

Zhang, JC ^{[1
]}

Matteucci, MD ^{[1
]}

机构：

[1] Gilead Sci Inc, Foster City, CA 94404 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 15期

关键词：

D O I：

10.1016/S0960-894X(99)00358-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A N-acylsulfamide linked thymidine dinucleoside was synthesized and incorporated into an oligonucleotide (ON). The interest is in a linkage analog that has a higher pKa relative to a phosphodiester and when incorporated into ONs is capable of helix formation with complementary RNA. The hybridization property of the resultant ON with RNA was shown to result in significant destabilization. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：2213 / 2216

页数：4

相关论文

共 15 条

[1] TRANSBILAYER MOVEMENT OF BILE-ACIDS IN MODEL MEMBRANES [J].

CABRAL, DJ ;

SMALL, DM ;

LILLY, HS ;

HAMILTON, JA .

BIOCHEMISTRY, 1987, 26 (07) :1801-1804

[2]

CROOKE ST, 1995, PHARM NEWS, V2, P8

[3] The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes [J].

Freier, SM ;

Altmann, KH .

NUCLEIC ACIDS RESEARCH, 1997, 25 (22) :4429-4443

[4] OLIGONUCLEOTIDES WITH A NUCLEASE-RESISTANT SULFUR-BASED LINKAGE [J].

HUIE, EM ;

KIRSHENBAUM, MR ;

TRAINOR, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4569-4570

[5] INTERACTIONS OF DICARBOXYLIC PORPHYRINS WITH UNILAMELLAR LIPIDIC VESICLES - DRASTIC EFFECTS OF PH AND CHOLESTEROL ON KINETICS [J].

KUZELOVA, K ;

BRAULT, D .

BIOCHEMISTRY, 1995, 34 (35) :11245-11255

[6]

MATTEUCCI MD, 1996, NATURE S20, V384

[7] Synthesis of sulfamide linked dinucleotide analogues [J].

Micklefield, J ;

Fettes, KJ .

TETRAHEDRON LETTERS, 1997, 38 (30) :5387-5390

[8]

PATAI S, 1901, CHEM SULFONIC ACIDS, P253

[9] NUCLEAR MAGNETIC-RESONANCE DETERMINATIONS OF PERMEATION COEFFICIENTS FOR MALEIC-ACID IN PHOSPHOLIPID-VESICLES [J].

PRESTEGARD, JH ;

CRAMER, JA ;

VISCIO, DB .

BIOPHYSICAL JOURNAL, 1979, 26 (03) :575-584

[10]

SANGER W, 1984, PRINCIPLES NUCL ACID, P230