Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification

Thangaiah Subramanian; Karunai Leela Subramanian; Manjula Sunkara; Fredrick O. Onono; Andrew J. Morris; H. Peter Spielmann

doi:10.1002/jlcr.3049

Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification

Thangaiah Subramanian
, Karunai Leela Subramanian
, Manjula Sunkara
, Fredrick O. Onono
, Andrew J. Morris
, H. Peter Spielmann

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

4 Scopus citations

Abstract

A Wittig reaction employing Li(CD₃)₂CP(C ₆H₅)₃ was used to prepare d₆- farnesol and d₆-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d₅ was used to prepare the unnatural isoprenoid analogues d₅-anilinogeraniol and d₅-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis. Deuterated isoprenols d₆-farnesol, d₆-geranylgeraniol, d₅- anilinogeraniol, d₅-anilinofarnesol and their corresponding diphosphates and cysteine thioethers were synthesized. These compounds are useful as stable-isotope labeled standards for quantitative mass spectrometric analysis.

Original language	English
Pages (from-to)	370-375
Number of pages	6
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	56
Issue number	8
DOIs	https://doi.org/10.1002/jlcr.3049
State	Published - Jun 30 2013

Funding

Funders	Funder number
National Institutes of Health (NIH)	P20 GM103527, R01 GM50388, R01 GM66152
National Institute of General Medical Sciences	R01GM066152

Keywords

AFPP
AGPP
FPP
FTase
GGPP
mass standards
protein prenylation
stable labeled synthesis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/jlcr.3049

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@article{1442f9e81726492b89be7c2b3fea6a22,

title = "Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification",

abstract = "A Wittig reaction employing Li(CD3)2CP(C 6H5)3 was used to prepare d6- farnesol and d6-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d5 was used to prepare the unnatural isoprenoid analogues d5-anilinogeraniol and d5-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis. Deuterated isoprenols d6-farnesol, d6-geranylgeraniol, d5- anilinogeraniol, d5-anilinofarnesol and their corresponding diphosphates and cysteine thioethers were synthesized. These compounds are useful as stable-isotope labeled standards for quantitative mass spectrometric analysis.",

keywords = "AFPP, AGPP, FPP, FTase, GGPP, mass standards, protein prenylation, stable labeled synthesis",

author = "Thangaiah Subramanian and Subramanian, \{Karunai Leela\} and Manjula Sunkara and Onono, \{Fredrick O.\} and Morris, \{Andrew J.\} and Spielmann, \{H. Peter\}",

year = "2013",

month = jun,

day = "30",

doi = "10.1002/jlcr.3049",

language = "English",

volume = "56",

pages = "370--375",

number = "8",

}

Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification. / Subramanian, Thangaiah; Subramanian, Karunai Leela; Sunkara, Manjula et al.
In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 56, No. 8, 30.06.2013, p. 370-375.

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

TY - JOUR

T1 - Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification

AU - Subramanian, Thangaiah

AU - Subramanian, Karunai Leela

AU - Sunkara, Manjula

AU - Onono, Fredrick O.

AU - Morris, Andrew J.

AU - Spielmann, H. Peter

PY - 2013/6/30

Y1 - 2013/6/30

N2 - A Wittig reaction employing Li(CD3)2CP(C 6H5)3 was used to prepare d6- farnesol and d6-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d5 was used to prepare the unnatural isoprenoid analogues d5-anilinogeraniol and d5-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis. Deuterated isoprenols d6-farnesol, d6-geranylgeraniol, d5- anilinogeraniol, d5-anilinofarnesol and their corresponding diphosphates and cysteine thioethers were synthesized. These compounds are useful as stable-isotope labeled standards for quantitative mass spectrometric analysis.

AB - A Wittig reaction employing Li(CD3)2CP(C 6H5)3 was used to prepare d6- farnesol and d6-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d5 was used to prepare the unnatural isoprenoid analogues d5-anilinogeraniol and d5-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis. Deuterated isoprenols d6-farnesol, d6-geranylgeraniol, d5- anilinogeraniol, d5-anilinofarnesol and their corresponding diphosphates and cysteine thioethers were synthesized. These compounds are useful as stable-isotope labeled standards for quantitative mass spectrometric analysis.

KW - AFPP

KW - AGPP

KW - FPP

KW - FTase

KW - GGPP

KW - mass standards

KW - protein prenylation

KW - stable labeled synthesis

UR - https://www.scopus.com/pages/publications/84880776374

UR - https://www.scopus.com/pages/publications/84880776374#tab=citedBy

U2 - 10.1002/jlcr.3049

DO - 10.1002/jlcr.3049

M3 - Article

C2 - 24285475

AN - SCOPUS:84880776374

SN - 0362-4803

VL - 56

SP - 370

EP - 375

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

IS - 8

ER -

Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification

Abstract

Funding

Keywords

ASJC Scopus subject areas

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