Synthetic elaboration of native DNA by RASS (SenDr)

Dillon T. Flood; Kyle W. Knouse; Julien C. Vantourout; Seiya Kitamura; Brittany B. Sanchez; Emily J. Sturgell; Jason S. Chen; Dennis W. Wolan; Phil S. Baran; Philip E. Dawson

doi:10.1021/acscentsci.0c00680

Synthetic elaboration of native DNA by RASS (SenDr)

Dillon T. Flood, Kyle W. Knouse, Julien C. Vantourout, Seiya Kitamura, Brittany B. Sanchez, Emily J. Sturgell, Jason S. Chen, Dennis W. Wolan, Phil S. Baran, Philip E. Dawson

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

9 Scopus citations

Abstract

Controlled site-specific bioconjugation through chemical methods to native DNA remains an unanswered challenge. Herein, we report a simple solution to achieve this conjugation through the tactical combination of two recently developed technologies: one for the manipulation of DNA in organic media and another for the chemoselective labeling of alcohols. Reversible adsorption of solid support (RASS) is employed to immobilize DNA and facilitate its transfer into dry acetonitrile. Subsequent reaction with P(V)-based Ψ reagents takes place in high yield with exquisite selectivity for the exposed 3′ or 5′ alcohols on DNA. This two-stage process, dubbed SENDR for Synthetic Elaboration of Native DNA by RASS, can be applied to a multitude of DNA conformations and sequences with a variety of functionalized Ψ reagents to generate useful constructs.

Original language	English (US)
Pages (from-to)	1789-1799
Number of pages	11
Journal	ACS Central Science
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/acscentsci.0c00680
State	Published - Oct 28 2020
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1021/acscentsci.0c00680

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title = "Synthetic elaboration of native DNA by RASS (SenDr)",

abstract = "Controlled site-specific bioconjugation through chemical methods to native DNA remains an unanswered challenge. Herein, we report a simple solution to achieve this conjugation through the tactical combination of two recently developed technologies: one for the manipulation of DNA in organic media and another for the chemoselective labeling of alcohols. Reversible adsorption of solid support (RASS) is employed to immobilize DNA and facilitate its transfer into dry acetonitrile. Subsequent reaction with P(V)-based Ψ reagents takes place in high yield with exquisite selectivity for the exposed 3′ or 5′ alcohols on DNA. This two-stage process, dubbed SENDR for Synthetic Elaboration of Native DNA by RASS, can be applied to a multitude of DNA conformations and sequences with a variety of functionalized Ψ reagents to generate useful constructs.",

author = "Flood, {Dillon T.} and Knouse, {Kyle W.} and Vantourout, {Julien C.} and Seiya Kitamura and Sanchez, {Brittany B.} and Sturgell, {Emily J.} and Chen, {Jason S.} and Wolan, {Dennis W.} and Baran, {Phil S.} and Dawson, {Philip E.}",

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T1 - Synthetic elaboration of native DNA by RASS (SenDr)

AU - Flood, Dillon T.

AU - Knouse, Kyle W.

AU - Vantourout, Julien C.

AU - Kitamura, Seiya

AU - Sanchez, Brittany B.

AU - Sturgell, Emily J.

AU - Chen, Jason S.

AU - Wolan, Dennis W.

AU - Baran, Phil S.

AU - Dawson, Philip E.

PY - 2020/10/28

Y1 - 2020/10/28

N2 - Controlled site-specific bioconjugation through chemical methods to native DNA remains an unanswered challenge. Herein, we report a simple solution to achieve this conjugation through the tactical combination of two recently developed technologies: one for the manipulation of DNA in organic media and another for the chemoselective labeling of alcohols. Reversible adsorption of solid support (RASS) is employed to immobilize DNA and facilitate its transfer into dry acetonitrile. Subsequent reaction with P(V)-based Ψ reagents takes place in high yield with exquisite selectivity for the exposed 3′ or 5′ alcohols on DNA. This two-stage process, dubbed SENDR for Synthetic Elaboration of Native DNA by RASS, can be applied to a multitude of DNA conformations and sequences with a variety of functionalized Ψ reagents to generate useful constructs.

AB - Controlled site-specific bioconjugation through chemical methods to native DNA remains an unanswered challenge. Herein, we report a simple solution to achieve this conjugation through the tactical combination of two recently developed technologies: one for the manipulation of DNA in organic media and another for the chemoselective labeling of alcohols. Reversible adsorption of solid support (RASS) is employed to immobilize DNA and facilitate its transfer into dry acetonitrile. Subsequent reaction with P(V)-based Ψ reagents takes place in high yield with exquisite selectivity for the exposed 3′ or 5′ alcohols on DNA. This two-stage process, dubbed SENDR for Synthetic Elaboration of Native DNA by RASS, can be applied to a multitude of DNA conformations and sequences with a variety of functionalized Ψ reagents to generate useful constructs.

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Synthetic elaboration of native DNA by RASS (SenDr)

Abstract

ASJC Scopus subject areas

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