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New Synthetic Methods for Phosphate Labeling

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Abstract

The complexity of phosphorylation pathways and their downstream effects is vast. Synthetic chemistry has been working side by side with biology to develop phosphate labels for biological processes involving phosphorylated compounds. This chapter discusses recently employed methods for the preparation of several phosphate labels. Synthesis of biomolecules and their analogs and other useful or potentially useful phosphate derivatives is discussed.

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Abbreviations

A:

Adenosine

Ade:

Adenine

ATP:

Adenosine triphosphate

B:

Nucleobase

BMF4TPA:

Bis(difluoromethylene)triphosphoric acid

BMT:

Bismethylene triphosphate

Boc:

Tert-Butyloxycarbonyl

Bop:

Bis(2-oxo-3-oxazolidinyl)phosphinic

BP :

Protected nucleobase

BTT:

5-Benzylthio-1-H-tetrazole

C:

Cytosine

CDI:

Carbodiimidazole

CE:

β-Cyanoethyl

CEM:

Cyanooxymethyl

CMPT:

N-(cyanomethyl)pyrrolidinium triflate

CPG:

Controlled pore glass

CTP:

Cytidine triphosphate

Cyt:

Cytidine

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCA:

Dichloroacetic acid

DCI:

4,5-Dicyanoimidazole

DEAE:

Diethylaminoethyl

DIAD:

Diisopropyl azodicarboxylate

DIPEA:

Diisopropylethylamine

DMAN:

1,8-Bis-(dimethylamino)naphthalene

DMF:

N,N-dimethylformamide

DMS:

Dimethylsulfide

DMTr:

4,4′-Dimethoyxltrityl

DTD:

N,N-dimethylthiuram disulfide

EC50 :

Half maximal effective concentration

EDC/EDCI:

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

ETT:

5-(Ethylthio)-1H-tetrazole

Fm:

9-Fluorenylmethyl

Fmoc:

Fluorenylmethyloxycarbonyl

G:

Guanosine

Gua:

Guanine

IC50 :

Half maximal inhibitor concentration

IEX-HPLC:

Ion-exchange high performance liquid chromatography

KHMDS:

Hexamethyldisilazide

LTMPA:

Lithium 2,2,6,6-tetramethylpiperidine amide

NHS:

N-hydroxysuccinimide

NMP:

Nucleoside monophosphate

Npn :

Nucleoside polyphosphate

NpnN:

Dinucleotide polyphosphate

NPP:

Nucleotide pyrophosphatase/phosphodiesterase

Ns:

Nosyl

NTP:

Nucleoside triphosphate

NTP:

Nucleoside triphosphate

Nuc:

Nucleotide or nucleoside

ODN:

Oligodeoxynucleotides

ORN:

Oligoribonucleotide

OTP:

Oxathiaphospholane

PEP:

Phosphoenolpyruvate

Pip:

Piperidine

PK:

Pyruvate dinase

ppGpp:

Guanosin-3′,5′-bispyrophosphate

ppp:

RNA 5′-triphosphate RNAs

PRR:

Pattern recognition receptors

Py:

Pyridine

RP18:

Reverse phase C18

RSH:

RelA-SpoT homolog

SAX:

Strong anion exchange

T:

Thymine

TBAF:

Tetrabutylammonium fluoride

TBHP:

tert-Butylhydroperoxide

TBS:

tert-Butyldimethylsilyl

TEA:

Triethylamine

TEAB:

Triethylammonium bicarbonate

Tf:

Trifluoromethylsulfonyl

THF:

Tetrahydrofuran

Thy:

Thymidine

TMS:

Trimethylsilyl

Tr:

2,4,6-Triisopropylbenzenesulfonyl

Ts:

p-Toluenesulfonyl

U:

Uridine

Ura:

Uracil

UTP:

Uridine triphosphate

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Acknowledgements

Funding was provided by Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (Grant No. SNF, PP00P2_157607) and HFSP Organization (Grant No. RGP0025/2016).

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  1. Institute of Organic Chemistry, Albertstrasse 21, 79104, Freiburg im Breisgau, Germany

    Amit K. Dutta, Ilya Captain & Henning Jacob Jessen

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  1. Amit K. Dutta
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Correspondence to Henning Jacob Jessen.

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This article is part of the Topical Collection “Phosphate Labeling and Sensing in Chemical Biology”; edited by Henning Jessen.

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Dutta, A.K., Captain, I. & Jessen, H.J. New Synthetic Methods for Phosphate Labeling. Top Curr Chem (Z) 375, 51 (2017). https://doi.org/10.1007/s41061-017-0135-6

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