Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite

Russell Clayton; Michael L. Davis; Wei Li; William Fraser; Christopher Ramsden

doi:10.24820/ark.5550190.p010.075

Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite

Russell Clayton, Michael L. Davis, Wei Li, William Fraser, Christopher Ramsden

Research output: Contribution to journal › Article › peer-review

Abstract

Pyridine-stretched 2!-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer’s sugar (2!-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer’s sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2!-deoxyadenosine (strA) and pyridine-stretched 2!-deoxy-diaminopurine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Original language	English
Article number	OR-10075VP
Pages (from-to)	87-104
Number of pages	18
Journal	Arkivoc
Volume	2017
Issue number	3
DOIs	https://doi.org/10.24820/ark.5550190.p010.075
Publication status	Published - 10 Apr 2017

Bibliographical note

© The authors. Creative Commons License Deed; Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) https://creativecommons.org/licenses/by-nc/4.0/

Funding: Scotia Pharmaceuticals; Royal Society; and EPSRC Mass Spectrometry Cenre for high-resolution mass spectra.

Copies of 1H and 13C NMR spectra are provided as supplementary material.

Keywords

5-aminoimidazoles
Hoffer’s sugar
pyridine-stretched purines
hypoxanthosine
phosphoramidite

Access to Document

10.24820/ark.5550190.p010.075Licence: CC BY-NC 3.0

Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite
© The authors. Creative Commons License Deed; Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) https://creativecommons.org/licenses/by-nc/4.0/
Final published version, 392 KBLicence: CC BY-NC 3.0

Cite this

@article{b096c89d9a8d4838bbdb7bf17ba30b36,

title = "Preparation of pyridine-stretched 2{\textquoteright}-deoxyhypoxanthosine phosphoramidite",

abstract = "Pyridine-stretched 2!-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer{\textquoteright}s sugar (2!-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer{\textquoteright}s sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2!-deoxyadenosine (strA) and pyridine-stretched 2!-deoxy-diaminopurine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.",

keywords = "5-aminoimidazoles, Hoffer{\textquoteright}s sugar, pyridine-stretched purines, hypoxanthosine, phosphoramidite",

author = "Russell Clayton and Davis, {Michael L.} and Wei Li and William Fraser and Christopher Ramsden",

note = "{\textcopyright} The authors. Creative Commons License Deed; Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) https://creativecommons.org/licenses/by-nc/4.0/ Funding: Scotia Pharmaceuticals; Royal Society; and EPSRC Mass Spectrometry Cenre for high-resolution mass spectra. Copies of 1H and 13C NMR spectra are provided as supplementary material.",

year = "2017",

month = apr,

day = "10",

doi = "10.24820/ark.5550190.p010.075",

language = "English",

volume = "2017",

pages = "87--104",

journal = "Arkivoc",

issn = "1551-7004",

publisher = "Arkat USA",

number = "3",

}

TY - JOUR

T1 - Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite

AU - Clayton, Russell

AU - Davis, Michael L.

AU - Li, Wei

AU - Fraser, William

AU - Ramsden, Christopher

N1 - © The authors. Creative Commons License Deed; Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) https://creativecommons.org/licenses/by-nc/4.0/ Funding: Scotia Pharmaceuticals; Royal Society; and EPSRC Mass Spectrometry Cenre for high-resolution mass spectra. Copies of 1H and 13C NMR spectra are provided as supplementary material.

PY - 2017/4/10

Y1 - 2017/4/10

N2 - Pyridine-stretched 2!-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer’s sugar (2!-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer’s sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2!-deoxyadenosine (strA) and pyridine-stretched 2!-deoxy-diaminopurine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

AB - Pyridine-stretched 2!-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer’s sugar (2!-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer’s sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2!-deoxyadenosine (strA) and pyridine-stretched 2!-deoxy-diaminopurine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

KW - 5-aminoimidazoles

KW - Hoffer’s sugar

KW - pyridine-stretched purines

KW - hypoxanthosine

KW - phosphoramidite

UR - http://www.arkat-usa.org/get-file/59687/

UR - http://www.scopus.com/inward/record.url?scp=85020721460&partnerID=8YFLogxK

U2 - 10.24820/ark.5550190.p010.075

DO - 10.24820/ark.5550190.p010.075

M3 - Article

AN - SCOPUS:85075398086

SN - 1551-7004

VL - 2017

SP - 87

EP - 104

JO - Arkivoc

JF - Arkivoc

IS - 3

M1 - OR-10075VP

ER -

Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this