Polymer-bound reagents for the introduction of spacer-modified biotin labels

被引：6

作者：

Herforth, C

Heidler, P

Franke, S

Link, A

机构：

[1] Univ Marburg, Fac Pharm, D-35032 Marburg, Germany

[2] Univ Hamburg, Fac Chem, D-20146 Hamburg, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 11期

关键词：

D O I：

10.1016/j.bmc.2004.03.038

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We have developed a method for the chemoselective introduction of spacer modified biotin labels into unprotected multifunctional amines. A range of novel biotin spacer conjugates attached to a polymer-bound sulfonamide anchor was prepared using established amide bond forming procedures. After chemical transformation of the attachment site by alkylation, the resulting reactive species were utilized as N-selective polymer-supported biotinylation reagents. The labeled compounds, obtained in good to excellent yield and purity, are free of residual biotin and possess a custom tailored distance from the immobilization site being especially suited for the immobilization on streptavidin-functionalized dextran layers of surface plasmon resonance detector chips. In addition, derivatives displaying a phenyl group were synthesized in order to demonstrate the versatility of the procedure for the simultaneous introduction of spacer-modified biotin and a UV-light absorbing moiety. The formation of biotin sulfoxides in the presence of in situ generated peroxides was investigated and is discussed. Our results suggest that this derivatization technique is a useful addition to the existing biotin labeling protocols. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2895 / 2902

页数：8

共 39 条

[21] AN ELECTRODE MODIFIED WITH POLYMER-BOUND DOPAMINE WHICH CATALYZES NADH OXIDATION
DEGRAND, C
MILLER, LL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) : 5728 - 5732
[22] REPETITIVE PEPTIDE-SYNTHESIS WITH INSOLUBLE POLYMER-BOUND REAGENTS AND SOLUBILIZING MACROMOLECULAR PEPTIDE CARRIERS
HEUSEL, G
BOVERMANN, G
GOHRING, W
JUNG, G
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (09): : 642 - 643
[23] CONCURRENT CATALYTIC REDUCTION STOICHIOMETRIC OXIDATION USING OLIGOMERICALLY LIGATED CATALYSTS AND POLYMER-BOUND REAGENTS
BERGBREITER, DE
CHANDRAN, R
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 72 - ORN
[24] CONCURRENT CATALYTIC REDUCTION STOICHIOMETRIC OXIDATION USING OLIGOMERICALLY LIGATED CATALYSTS AND POLYMER-BOUND REAGENTS
BERGBREITER, DE
CHANDRAN, R
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (16) : 4792 - 4793
[25] SYNTHESIS OF SPACER-MODIFIED POLYMER SUPPORTS WITH THE AID OF ETHERIFICATION AND PHASE-TRANSFER CATALYTIC ACTIVITY OF PHOSPHONIUM SALTS DERIVED FROM THE POLYMER SUPPORTS
TOMOI, M
SHIIKI, S
KAKIUCHI, H
MAKROMOLEKULARE CHEMIE-MACROMOLECULAR CHEMISTRY AND PHYSICS, 1986, 187 (02): : 357 - 365
[26] ARYNIC SPECIES .2. TOSYL AND TRIAZENE AS LEAVING GROUP IN THE GENERATION OF ARYNES FROM POLYMER-BOUND REAGENTS
GAVINA, F
LUIS, SV
FERRER, P
COSTERO, AM
GIL, P
TETRAHEDRON, 1986, 42 (20) : 5641 - 5648
[27] Using polymer-bound bi(cycloSaligenyl) phosphitylating reagents for the synthesis of nucleoside mono-, di-, and triphosphates
Ahmadibeni, Yousef
Tiwari, Rakesh
Parang, Keykavous
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[28] Polymer-Bound Triphenylphosphine and 4,4′-Dinitroazobenzene as a Coupling Reagents for Chromatography-Free Esterification Reaction
Das, Diparjun
Rajkumari, Kalyani
Rokhum, Lalthazuala
CURRENT ORGANIC SYNTHESIS, 2019, 16 (07) : 1024 - 1031
[29] Polymer-bound p-alkoxybenzyl trichloracetimidates:: Reagents for the protection of alcohols as benzyl ethers on solid-phase
Hanessian, S
Xie, F
TETRAHEDRON LETTERS, 1998, 39 (08) : 733 - 736
[30] POLYMER-BOUND MIXED CARBOXYLIC DITHIOCARBAMIC ANHYDRIDES - A NEW CLASS OF SELECTIVE AND RECYCLABLE SOLID-PHASE ACYLATING REAGENTS
HARIDASAN, VK
AJAYAGHOSH, A
PILLAI, VNR
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2662 - 2665

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