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Chemistry
Heterocyclic Building Blocks
Pyrimidines
tetrahydrofuran-pyrimidine
Adenosine
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tetrahydrofuran-pyrimidine
2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3,4-diol

[ CAS No. 58-61-7 ] {[proInfo.proName]}

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Chemical Structure| 58-61-7
Chemical Structure| 58-61-7
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Product Citations

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Kirk M. Atkinson ; Bradley D. Smith ; DOI:

Abstract: Ratiometric fluorescent assays have a built-in correction factor which enhances assay accuracy and reliability. We have developed fluorescent ratiometric supramolecular tandem assays for and phytase enzymes using a mixture of three molecular components. One of the molecules is a tetra-cationic fluorescence quencher called CalixPyr which can bind and quench the polyanionic fluorophore, CMP, that emits at 430 nm. Polyphosphates can disrupt the CMP/CalixPyr complex and alter the fluorescence intensity (responsive signal). CalixPyr has no effect on the fluorescence emission of cationic pentamethine cyanine fluorophore, cCy5, which emits at 665 nm and acts as a non-responsive reference signal. The continuous ratiometric fluorescent assay for alkaline monitored hydrolytic consumption of (ATP). The continuous ratiometric fluorescent assay for phytase activity monitored hydrolytic consumption of phytate. With further development this latter assay may be useful for high throughput assessment of phytase activity in individual batches of fortified animal feed. It is likely that the three-molecule mixture (CMP, CalixPyr, cCy5) can become a general assay platform for other enzymes that catalyse addition/removal of phosphate groups from appropriate molecular substrates.

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Zhou, Jujun ; Deng, Youchao ; Iyamu, Iredia D. , et al. DOI: PubMed ID:

Abstract: S-Adenosyl-L-methionine (SAM) analogs are adaptable tools for studying and therapeutically inhibiting SAM-dependent methyltransferases (MTases). Some MTases play significant roles in host-pathogen interactions, one of which is Clostridioides difficile-specific DNA adenine MTase (CamA). CamA is needed for efficient sporulation and alters persistence in the colon. To discover potent and selective CamA inhibitors, we explored modifications of the solvent-exposed edge of the SAM adenosine moiety. Starting from the two parental compounds (6e and 7), we designed an adenosine analog (11a) carrying a 3-phenylpropyl moiety at the adenine N6-amino group, and a 3-(cyclohexylmethyl guanidine)-Et moiety at the sulfur atom off the ribose ring. Compound 11a (IC50 = 0.15 μM) is 10x and 5x more potent against CamA than 6e and 7, resp. The structure of the CamA-DNA-inhibitor complex revealed that 11a adopts a U-shaped conformation, with the two branches folded toward each other, and the aliphatic and aromatic rings at the two ends interacting with one another. 11a occupies the entire hydrophobic surface (apparently unique to CamA) next to the adenosine binding site. Our work presents a hybrid knowledge-based and fragment-based approach to generating CamA inhibitors that would be chem. agents to examine the mechanism(s) of action and therapeutic potentials of CamA in C. difficile infection.

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Product Details of [ 58-61-7 ]

CAS No. :58-61-7 MDL No. :MFCD00005752
Formula : C10H13N5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :OIRDTQYFTABQOQ-KQYNXXCUSA-N
M.W : 267.24 Pubchem ID :60961
Synonyms :
Adenine riboside;D-Adenosine;NSC 627048;NSC 7652
Chemical Name :(2R,3R,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Safety of [ 58-61-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58-61-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 58-61-7 ]
  • Downstream synthetic route of [ 58-61-7 ]

[ 58-61-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 58-61-7 ]
  • [ 34408-14-5 ]
YieldReaction ConditionsOperation in experiment
52% With N-chloro-succinimide; acetic acid In N,N-dimethyl-formamide at 20℃; for 48 h; Procedure 2: Adenosine (1.09g, 4.08 mmol) was suspended in DMF (50 mL) and glacial acetic acid (10 mL) was added. A solution of N-chlorosuccinimide (2 g, 15 mmol) in DMF (15 mL) was added dropwise. The reaction mixture was stirred at rt for 48 hours and the volatiles were evaporated in vacuo to give yellow gum. The crude was absorbed on silica and purified by silica gel CC (packed in 5percent MeOHICHC13, eluted with 7percent MeOHICHC13) to yield a white powder (0.65 g, 52 percent).‘H NIVIR (500 MHz, DMSO-d6) 8.16 (s, 1H, H-2), 7.55 (br s, 2H, NH2), 5.86 (d, J = 6.8 Hz, 1H, Hi’), 5.48 (d, J 6.2 Hz, iH, 2’OH), 5.45 (d, J 4.0 Hz, iH, 5’-OH), 5.23 (d, J4.6 Hz, iH, 3’OH), 5.08-5.06 (m, iH, H-2’), 4.23-4.i8 (m, iH, H3’), 4.01-3.96 (m, iH, H4’),3.72-3.65 (m, iH, H5’), 3.57-3.50 (m, iH, H5’).
Reference： [1] Patent: WO2017/207989, 2017, A1, . Location in patent: Page/Page column 55; 56
[2] Journal of Organic Chemistry, 1981, vol. 46, # 13, p. 2819 - 2823
[3] Nucleosides, nucleotides and nucleic acids, 2002, vol. 21, # 8-9, p. 599 - 617
  • 2
  • [ 7732-18-5 ]
  • [ 58-61-7 ]
  • [ 34408-14-5 ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid In methanol; N,N-dimethyl-formamide Method B
to a solution of adenosine (1.09 g, 4.1 mmol) in DMF (50 mL) and AcOH (10 mL) was added N-Chlorosuccinamide (NCS, 2.0 g, 15 mmol).
The reaction mixture was stirred at room temperature for 6 days.
The solvents were evaporated to dryness and the residue was purified by HPLC on a C-18 reverse phase column using MeOH:AcOH:H2 O (18:1:18, v/v) to give 0.8 g (65percent) of 2, which was identical to the title compound prepared by Method A.
Reference： [1] Patent: US4861873, 1989, A,

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Heterocyclic Building Blocks
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2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3,4-diol
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tetrahydrofuran-pyrimidine
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2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3,4-diol
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