15N-Multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]-labeled adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine

José Luis Abad; Barbara L. Gaffney; Roger A. Jones

doi:https://doi.org/10.1021/jo982372k

¹⁵N-Multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,NH₂-¹⁵N₃]-labeled adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine

José Luis Abad, Barbara L. Gaffney, Roger A. Jones

School of Arts and Sciences, Chemistry & Chemical Biology

Rutgers, The State University

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

29 Scopus citations

Abstract

We report a high-yield route to the following specifically ¹⁵N- and ¹³C-multilabeled nucleosides: [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,NH₂- ¹⁵N₃]-adenosine; [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,NH₂-¹⁵N₃]- guanosine; [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,NH₂-¹⁵N₃]-2'- deoxyadenosine; [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,-NH₂-¹⁵N₃]-2'- deoxyguanosine. In each set, the ¹³C2 atom functions as a 'tag' that allows the ¹⁵N1 and ¹⁵N3 atoms to be unambiguously differentiated from the untagged versions in ¹⁵N NMR of RNA or DNA fragments. The key intermediate of this synthetic strategy for both the adenine and guanine nucleosides is [NH₂,CONH₂-¹⁵N₂]-5-amino-4-imidazolecarboxamide. The [2-¹³C]-label is added through a ring closure using [¹³C]-sodium ethyl xanthate (NaS¹³CSOEt). Enzymatic transglycosylation of either multilabeled 6- chloropurine or multilabeled 2-mercaptohypoxanthine and a final reaction with ¹⁵NH₃ give the adenine and guanine nucleosides. This is the first report of a [3-¹⁵N]-labeled guanine nucleoside.

Original language	English (US)
Pages (from-to)	6575-6582
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	64
Issue number	18
DOIs	https://doi.org/10.1021/jo982372k
State	Published - Sep 3 1999

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Organic Chemistry

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@article{463d0c4578b44527aa9ad003e7819125,

title = "15N-Multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]-labeled adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine",

abstract = "We report a high-yield route to the following specifically 15N- and 13C-multilabeled nucleosides: [1,3,NH2-15N3]- and [2-13C-1,3,NH2- 15N3]-adenosine; [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]- guanosine; [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]-2'- deoxyadenosine; [1,3,NH2-15N3]- and [2-13C-1,3,-NH2-15N3]-2'- deoxyguanosine. In each set, the 13C2 atom functions as a 'tag' that allows the 15N1 and 15N3 atoms to be unambiguously differentiated from the untagged versions in 15N NMR of RNA or DNA fragments. The key intermediate of this synthetic strategy for both the adenine and guanine nucleosides is [NH2,CONH2-15N2]-5-amino-4-imidazolecarboxamide. The [2-13C]-label is added through a ring closure using [13C]-sodium ethyl xanthate (NaS13CSOEt). Enzymatic transglycosylation of either multilabeled 6- chloropurine or multilabeled 2-mercaptohypoxanthine and a final reaction with 15NH3 give the adenine and guanine nucleosides. This is the first report of a [3-15N]-labeled guanine nucleoside.",

author = "Abad, {Jos{\'e} Luis} and Gaffney, {Barbara L.} and Jones, {Roger A.}",

year = "1999",

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doi = "https://doi.org/10.1021/jo982372k",

language = "English (US)",

volume = "64",

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journal = "Journal of Organic Chemistry",

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¹⁵N-Multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,NH₂-¹⁵N₃]-labeled adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine. / Abad, José Luis; Gaffney, Barbara L.; Jones, Roger A.

In: Journal of Organic Chemistry, Vol. 64, No. 18, 03.09.1999, p. 6575-6582.

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

TY - JOUR

T1 - 15N-Multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]-labeled adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine

AU - Abad, José Luis

AU - Gaffney, Barbara L.

AU - Jones, Roger A.

PY - 1999/9/3

Y1 - 1999/9/3

N2 - We report a high-yield route to the following specifically 15N- and 13C-multilabeled nucleosides: [1,3,NH2-15N3]- and [2-13C-1,3,NH2- 15N3]-adenosine; [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]- guanosine; [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]-2'- deoxyadenosine; [1,3,NH2-15N3]- and [2-13C-1,3,-NH2-15N3]-2'- deoxyguanosine. In each set, the 13C2 atom functions as a 'tag' that allows the 15N1 and 15N3 atoms to be unambiguously differentiated from the untagged versions in 15N NMR of RNA or DNA fragments. The key intermediate of this synthetic strategy for both the adenine and guanine nucleosides is [NH2,CONH2-15N2]-5-amino-4-imidazolecarboxamide. The [2-13C]-label is added through a ring closure using [13C]-sodium ethyl xanthate (NaS13CSOEt). Enzymatic transglycosylation of either multilabeled 6- chloropurine or multilabeled 2-mercaptohypoxanthine and a final reaction with 15NH3 give the adenine and guanine nucleosides. This is the first report of a [3-15N]-labeled guanine nucleoside.

AB - We report a high-yield route to the following specifically 15N- and 13C-multilabeled nucleosides: [1,3,NH2-15N3]- and [2-13C-1,3,NH2- 15N3]-adenosine; [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]- guanosine; [1,3,NH2-15N3]- and [2-13C-1,3,NH2-15N3]-2'- deoxyadenosine; [1,3,NH2-15N3]- and [2-13C-1,3,-NH2-15N3]-2'- deoxyguanosine. In each set, the 13C2 atom functions as a 'tag' that allows the 15N1 and 15N3 atoms to be unambiguously differentiated from the untagged versions in 15N NMR of RNA or DNA fragments. The key intermediate of this synthetic strategy for both the adenine and guanine nucleosides is [NH2,CONH2-15N2]-5-amino-4-imidazolecarboxamide. The [2-13C]-label is added through a ring closure using [13C]-sodium ethyl xanthate (NaS13CSOEt). Enzymatic transglycosylation of either multilabeled 6- chloropurine or multilabeled 2-mercaptohypoxanthine and a final reaction with 15NH3 give the adenine and guanine nucleosides. This is the first report of a [3-15N]-labeled guanine nucleoside.

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U2 - https://doi.org/10.1021/jo982372k

DO - https://doi.org/10.1021/jo982372k

M3 - Article

VL - 64

SP - 6575

EP - 6582

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -

¹⁵N-Multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH₂-¹⁵N₃]- and [2-¹³C-1,3,NH₂-¹⁵N₃]-labeled adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine

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