Guanosine 3',5'-bisdiphosphate
Guanosine 3',5'-bisdiphosphate (ppGpp) is a guanosine derivative that inhibits guanylate kinase. Guanosine 3',5'-bisdiphosphate binds to the β' subunit of plastid-encoded bacterial-type RNA polymerase, inhibits the catalytic activity of guanylate kinase, and regulates chloroplast translation and GTP biosynthesis. Guanosine 3',5'-bisdiphosphate acts as a plant chloroplast signaling molecule and a global bacterial regulator, and plays a role in microbial persistence. Guanosine 3',5'-bisdiphosphate is applicable to biosynthesis-related research.
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- CAS No.: 32452-17-8
- Formula: C10H17N5O17P4
- Molecular Weight:603.16
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Guanosine 3',5'-bisdiphosphate inhibits RNA synthesis of transcriptionally active chromosomes isolated from plant chloroplasts[1].
Guanosine 3',5'-bisdiphosphate binds to the β' subunit of the plastid-encoded bacterial-type RNA polymerase in plant chloroplasts[1].
Guanosine 3',5'-bisdiphosphate (ppGpp) accumulates in rel+ Escherichia coli K-12 under two stress conditions: amino acid starvation and glucose repression, and blocks mRNA transcriptional elongation. Transcriptional elongation is not inhibited in relA mutant strains that cannot produce ppGpp[3].
Guanosine 3',5'-bisdiphosphate potently inhibits the guanylate kinase activity of OsGKpm (ND45) in a concentration-dependent manner, with an IC50 of approximately 10 μM and a Ki of 2.8 μM; it inhibits the guanylate kinase activity of Bacillus subtilis GK with a Ki of 13 μM[2].
Guanosine 3',5'-bisdiphosphate inhibits the guanylate kinase activity of purified recombinant pea chloroplast GK with an IC50 of approximately 30 μM; it also inhibits the guanylate kinase activity of Arabidopsis thaliana chloroplast GK with an IC50 of approximately 50 μM[2].
Guanosine 3',5'-bisdiphosphate inhibits the activity of endogenous guanylate kinase in isolated pea chloroplast extracts and reduces the conversion of GMP to GDP and GTP[2].
Guanosine 3',5'-bisdiphosphate inhibits the deoxyguanylate kinase activity of purified recombinant rice chloroplast GK (OsGKpm (ND45)) in a concentration-dependent manner[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 32452-17-8
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Molecular Weight 603.16
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Formula C10H17N5O17P4
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SMILES
O=C1C(N=CN2[C@H]3[C@H](O)[C@H](OP(OP(O)(O)=O)(O)=O)[C@@H](COP(OP(O)(O)=O)(O)=O)O3)=C2N=C(N)N1
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Synonyms
ppGpp
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Yamburenko MV, et al. Abscisic acid affects transcription of chloroplast genes via protein phosphatase 2C-dependent activation of nuclear genes: repression by guanosine-3'-5'-bisdiphosphate and activation by sigma factor 5. The Plant journal : for cell and molecular biology. 2015 Jun;82(6):1030-1041. [Content Brief]
[2]. Nomura Y, et al. Diversity in guanosine 3',5'-bisdiphosphate (ppGpp) sensitivity among guanylate kinases of bacteria and plants. The Journal of biological chemistry. 2014 May 30;289(22):15631-41. [Content Brief]
[3]. Vogel U, et al. Effects of guanosine 3',5'-bisdiphosphate (ppGpp) on rate of transcription elongation in isoleucine-starved Escherichia coli. The Journal of biological chemistry. 1994 Jun 10;269(23):16236-41. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Guanosine 3',5'-bisdiphosphate Related Classifications
HY-114265 Related Classifications
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- Guanosine 3',5'-bisdiphosphate
- 32452-17-8
- ppGpp
- Nucleoside Antimetabolite/Analog
- Saccharomyces cerevisiae cytosolic guanylate kinase
- Synechococcus elongatus guanylate kinase
- pea chloroplast guanylate kinase
- Bacillus subtilis guanylate kinase
- stringent response
- rice chloroplast guanylate kinase
- Arabidopsis chloroplast guanylate kinase
- plastid-encoded bacterial-type RNA polymerase
- chloroplast gene transcription
- Escherichia coli guanylate kinase
- Inhibitor
- inhibitor
- inhibit