A novel structural class of photoswitchable oligonucleotide

EE Smith; JN McClean; LA Cooke; Jean-Louis Duprey; M McCourt; MM Fabani; James Tucker; JS Vyle

doi:10.1016/j.tetlet.2007.07.028

A novel structural class of photoswitchable oligonucleotide

EE Smith, JN McClean, LA Cooke, Jean-Louis Duprey, M McCourt, MM Fabani, James Tucker, JS Vyle

Chemistry

Research output: Contribution to journal › Article

1 Citation (Scopus)

Abstract

Directed Michaelis-Arbuzov reactions of support-bound internucleotide O-benzyl- or O-methyl-phosphite triesters with meta-phenylazobenzylamine or alkane-/glycol-linked alpha,omega-diamines were effected in the presence of iodine. The corresponding tritylated phosphoramidate-linked 11-mers were fully deprotected and released from the support under standard conditions and the fast- and slow-diastereoisomers of both the E- and the Z-meta-phenylazobenzyl-appended oligomers were readily resolved by RP-HPLC. The primary amine-functionalised oligonucleotides were either purified, detritylated and then finally treated with N-hydroxysuccinimidyl carboxylic acid ester derivatives of photoswitchable moieties (Route A) or first derivatised and then subsequently purified and detritylated (Route B). This latter route enabled resolution of fast- and slow-isomers of the trityl-on oligomers bearing novel photoswitchable azopyridine or 9-alkoxyanthracene moieties using RP-HPLC, following which the pure diastereoisomers were detritylated and characterised by MALDI-MS. (C) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6569-6572
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.028
Publication status	Published - 10 Sept 2007

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@article{650c0899cdb0417780bbf9380c0f0926,

title = "A novel structural class of photoswitchable oligonucleotide",

abstract = "Directed Michaelis-Arbuzov reactions of support-bound internucleotide O-benzyl- or O-methyl-phosphite triesters with meta-phenylazobenzylamine or alkane-/glycol-linked alpha,omega-diamines were effected in the presence of iodine. The corresponding tritylated phosphoramidate-linked 11-mers were fully deprotected and released from the support under standard conditions and the fast- and slow-diastereoisomers of both the E- and the Z-meta-phenylazobenzyl-appended oligomers were readily resolved by RP-HPLC. The primary amine-functionalised oligonucleotides were either purified, detritylated and then finally treated with N-hydroxysuccinimidyl carboxylic acid ester derivatives of photoswitchable moieties (Route A) or first derivatised and then subsequently purified and detritylated (Route B). This latter route enabled resolution of fast- and slow-isomers of the trityl-on oligomers bearing novel photoswitchable azopyridine or 9-alkoxyanthracene moieties using RP-HPLC, following which the pure diastereoisomers were detritylated and characterised by MALDI-MS. (C) 2007 Elsevier Ltd. All rights reserved.",

author = "EE Smith and JN McClean and LA Cooke and Jean-Louis Duprey and M McCourt and MM Fabani and James Tucker and JS Vyle",

year = "2007",

month = sep,

day = "10",

doi = "10.1016/j.tetlet.2007.07.028",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - A novel structural class of photoswitchable oligonucleotide

AU - Smith, EE

AU - McClean, JN

AU - Cooke, LA

AU - Duprey, Jean-Louis

AU - McCourt, M

AU - Fabani, MM

AU - Tucker, James

AU - Vyle, JS

PY - 2007/9/10

Y1 - 2007/9/10

N2 - Directed Michaelis-Arbuzov reactions of support-bound internucleotide O-benzyl- or O-methyl-phosphite triesters with meta-phenylazobenzylamine or alkane-/glycol-linked alpha,omega-diamines were effected in the presence of iodine. The corresponding tritylated phosphoramidate-linked 11-mers were fully deprotected and released from the support under standard conditions and the fast- and slow-diastereoisomers of both the E- and the Z-meta-phenylazobenzyl-appended oligomers were readily resolved by RP-HPLC. The primary amine-functionalised oligonucleotides were either purified, detritylated and then finally treated with N-hydroxysuccinimidyl carboxylic acid ester derivatives of photoswitchable moieties (Route A) or first derivatised and then subsequently purified and detritylated (Route B). This latter route enabled resolution of fast- and slow-isomers of the trityl-on oligomers bearing novel photoswitchable azopyridine or 9-alkoxyanthracene moieties using RP-HPLC, following which the pure diastereoisomers were detritylated and characterised by MALDI-MS. (C) 2007 Elsevier Ltd. All rights reserved.

AB - Directed Michaelis-Arbuzov reactions of support-bound internucleotide O-benzyl- or O-methyl-phosphite triesters with meta-phenylazobenzylamine or alkane-/glycol-linked alpha,omega-diamines were effected in the presence of iodine. The corresponding tritylated phosphoramidate-linked 11-mers were fully deprotected and released from the support under standard conditions and the fast- and slow-diastereoisomers of both the E- and the Z-meta-phenylazobenzyl-appended oligomers were readily resolved by RP-HPLC. The primary amine-functionalised oligonucleotides were either purified, detritylated and then finally treated with N-hydroxysuccinimidyl carboxylic acid ester derivatives of photoswitchable moieties (Route A) or first derivatised and then subsequently purified and detritylated (Route B). This latter route enabled resolution of fast- and slow-isomers of the trityl-on oligomers bearing novel photoswitchable azopyridine or 9-alkoxyanthracene moieties using RP-HPLC, following which the pure diastereoisomers were detritylated and characterised by MALDI-MS. (C) 2007 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2007.07.028

DO - 10.1016/j.tetlet.2007.07.028

M3 - Article

VL - 48

SP - 6569

EP - 6572

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

A novel structural class of photoswitchable oligonucleotide

Abstract

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