First aromatic electrophilic iodination reaction on the solid-phase:: Iodination of bioactive peptides

被引：13

作者：

Arsequell, G

Espuña, G

Valencia, G ^{[1
]}

Barluenga, J

Carlón, RP

González, JM

机构：

[1] Univ Oviedo, CSIC, Unidad Asociada, Inst Quim Organomet Enrique Moles, E-33071 Oviedo, Spain

[2] CSIC, Cid, Unit Glycoconjugate Chem, E-08034 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 40期

关键词：

amino acids and derivatives; halogenation; peptides and polypeptides; supported reagents/reactions;

D O I：

10.1016/S0040-4039(98)01604-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct iodination of Tyr residues of peptides anchored on solid supports was accomplished, for the first time, by aromatic electrophilic attack of iodonium ions provided by the IPy2BF4 reagent. Compatibility studies of the iodination with routine solid-phase synthesis protocols are reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

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页码：7393 / 7396

页数：4

相关论文

共 24 条

[1]

[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881

[2] Iodination of aromatic residues in peptides by reaction with IPy(2)BF(4) [J].

Barluenga, J ;

GarciaMartin, MA ;

Gonzalez, JM ;

Clapes, P ;

Valencia, G .

CHEMICAL COMMUNICATIONS, 1996, (13) :1505-1506

[3] ACID-MEDIATED REACTION OF BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE WITH AROMATIC-COMPOUNDS - A SELECTIVE AND GENERAL IODINATION METHOD [J].

BARLUENGA, J ;

GONZALEZ, JM ;

GARCIAMARTIN, MA ;

CAMPOS, PJ ;

ASENSIO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2058-2060

[4] POLYIODINATION ON BENZENE AT ROOM-TEMPERATURE A REGIOSELECTIVE SYNTHESIS OF DERIVATIVES [J].

BARLUENGA, J ;

GONZALEZ, JM ;

GARCIAMARTIN, MA ;

CAMPOS, PJ .

TETRAHEDRON LETTERS, 1993, 34 (24) :3893-3896

[5] Application of the sulfonamide functional group as an anchor for solid phase organic synthesis (SPOS) [J].

Beaver, KA ;

Siegmund, AC ;

Spear, KL .

TETRAHEDRON LETTERS, 1996, 37 (08) :1145-1148

[6] Preparation of radiolabeled peptides via an iodine exchange reaction [J].

Breslav, M ;

McKinney, A ;

Becker, JM ;

Naider, F .

ANALYTICAL BIOCHEMISTRY, 1996, 239 (02) :213-217

[7] FORMATION OF CARBON-CARBON BOND ON SOLID SUPPORT - APPLICATION OF THE STILLE REACTION [J].

DESHPANDE, MS .

TETRAHEDRON LETTERS, 1994, 35 (31) :5613-5614

[8] COMBINATORIAL DRUG DISCOVERY - WHICH METHODS WILL PRODUCE THE GREATEST VALUE [J].

ECKER, DJ ;

CROOKE, ST .

BIO-TECHNOLOGY, 1995, 13 (04) :351-360

[9] SOLID-PHASE CHEMISTRY - DIRECT MONITORING BY MATRIX-ASSISTED LASER-DESORPTION IONIZATION TIME-OF-FLIGHT MASS-SPECTROMETRY - A TOOL FOR COMBINATORIAL CHEMISTRY [J].

EGNER, BJ ;

LANGLEY, GJ ;

BRADLEY, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2652-2653

[10] BIARYL SYNTHESIS VIA SUZUKI COUPLING ON A SOLID SUPPORT [J].

FRENETTE, R ;

FRIESEN, RW .

TETRAHEDRON LETTERS, 1994, 35 (49) :9177-9180