A NEW PROTECTED ACYL PROTECTING GROUP FOR EXOCYCLIC AMINO FUNCTIONS OF NUCLEOBASES

被引：24

作者：

DREEFTROMP, CM

HOOGERHOUT, P

VANDERMAREL, GA

VANBOOM, JH

机构：

[1] Gorlaeus Laboratories, 2300 RA Leiden

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(00)94573-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Tert-butyldiphenylsilyloxymethyl)benzoyl chloride (SiOMB-Cl) reacts with the per-O-trimethylsilylated d-nucleosides C,G and A to give, after removal of the Si(Me)3 groups and 5'-O-protection with 4,4'-dimethoxytrityl chloride (DMT-Cl), the corresponding N-SiOMB-5'-O-DMT derivates, the SiOMB groups of which can easily be removed by fluoride ion. The SiOMB protected nucleosides proved to be suitable building units for the preparation of DNA fragments in solution and on a solid support. © 1990.

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页码：427 / 430

页数：4

相关论文

共 19 条

[1]

AMBROS V, 1978, J BIOL CHEM, V253, P5263

[2] CHARACTERIZATION OF THE DNA-PROTEIN COMPLEX AT THE TERMINI OF THE BACTERIOPHAGE PRD1 GENOME [J].

BAMFORD, DH ;

MINDICH, L .

JOURNAL OF VIROLOGY, 1984, 50 (02) :309-315

[3] SYNTHETIC PEPTIDES FROM 4 SEPARATE REGIONS OF THE POLIOVIRUS TYPE-1 CAPSID PROTEIN VP1 INDUCE NEUTRALIZING ANTIBODIES [J].

CHOW, M ;

YABROV, R ;

BITTLE, J ;

HOGLE, J ;

BALTIMORE, D .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1985, 82 (03) :910-914

[4]

DEROOIJ JFM, 1979, RECL TRAV CHIM PAY B, V98, P537

[5] GENERAL BASE-CATALYZED INTRAMOLECULAR TRANSESTERIFICATION [J].

FIFE, TH ;

BENJAMIN, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (06) :2059-2061

[6]

GAIT MJ, 1987, NUCLEOS NUCLEOT, V6, P341

[7] PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].

HANESSIAN, S ;

LAVALLEE, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977

[8] LOCATION OF THE SERINE RESIDUE INVOLVED IN THE LINKAGE BETWEEN THE TERMINAL PROTEIN AND THE DNA OF PHAGE-PHI-29 [J].

HERMOSO, JM ;

MENDEZ, E ;

SORIANO, F ;

SALAS, M .

NUCLEIC ACIDS RESEARCH, 1985, 13 (21) :7715-7728

[9] PRIMARY STRUCTURE, GENE ORGANIZATION AND POLYPEPTIDE EXPRESSION OF POLIOVIRUS RNA [J].

KITAMURA, N ;

SEMLER, BL ;

ROTHBERG, PG ;

LARSEN, GR ;

ADLER, CJ ;

DORNER, AJ ;

EMINI, EA ;

HANECAK, R ;

LEE, JJ ;

VANDERWERF, S ;

ANDERSON, CW ;

WIMMER, E .

NATURE, 1981, 291 (5816) :547-553

[10] A CONVENIENT APPROACH TOWARD THE PREPARATION OF NUCLEOPEPTIDES [J].

KUYLYEHESKIELY, E ;

TROMP, CM ;

LEFEBER, AWM ;

VANDERMAREL, GA ;

VANBOOM, JH .

TETRAHEDRON, 1988, 44 (20) :6515-6523