ChemInform Abstract: AMINONUCLEOSIDES AND THEIR DERIVATIVES. VI. A NEW SYNTHESIS OF 1,2,5‐TRI‐O‐ACYL‐3‐AZIDO‐3‐DEOXY‐β‐D‐RIBOFURANOSE

OZOLS, A. M.; Azhayev, Alex; Dyatkina, Natalia; Krayevsky, Alexander A.

doi:10.1002/chin.198044304

Cited by 2 publications

(4 citation statements)

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“…The synthetic route is outlined in Figure 2. Triflate 1 (20) was reacted with sodium azide in DMF (29) to give azide 2, accompanied by elimination to give the 3,4-dehydrosugar derivative in a similar proportion. Although this mixture could be separated, it was feasible to use the crude mixture for acetolysis of the protecting isopropylidene group (20) to give the epimeric diacetates 3.…”

Section: Resultsmentioning

confidence: 99%

“…Triflate 1 (20) was reacted with sodium azide in DMF (29) to give azide 2, accompanied by elimination to give the 3,4-dehydrosugar derivative in a similar proportion. Although this mixture could be separated, it was feasible to use the crude mixture for acetolysis of the protecting isopropylidene group (20) to give the epimeric diacetates 3. This mixture was satisfactory for use in the purination with the disilylated derivative of N 6 -benzoyladenine in the presence of trimethylsilyl triflate (30).…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of 3′-Amino-3′-deoxyATP:3-Azido-3-deoxy-1,2di-O-acetyl-5-O-(4-methylbenzoyl)-D-ribofuranose 3. Sodium azide (17.6 g, 270 mmol) was added to a solution of the triflate 1 [27 g, 61.4 mmol; synthesized as described previously (20)] in dry DMF (700 mL), and the mixture was stirred overnight at room temperature. The solvent was evaporated in Vacuo, and the residue was partitioned between water and diethyl ether.…”

Section: Methodsmentioning

confidence: 99%

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A Series of Related Nucleotide Analogues that Aids Optimization of Fluorescence Signals in Probing the Mechanism of P-Loop ATPases, Such as Actomyosin

Webb¹,

Reid²,

Munasinghe³

et al. 2004

Biochemistry

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We have synthesized a set of ATP and ADP analogues that have a fluorophore linked to the nucleotide via the 3'-position of the ribose moiety. Combinations of three different coumarins are each attached via different length linkers. A linker based on propylenediamine increases the separation between the nucleotide and fluorophore relative to that of the previously reported ethylenediamine-linked coumarin nucleotides [Webb, M. R., and Corrie, J. E. T. (2001) Biophys. J. 81, 1562-1569]. A synthesis of 3'-amino-3'-deoxyATP is described using a combination of chemical and enzymatic procedures, mostly from published methods for synthesis of this compound but with some modifications that improved the convenience of the experimental procedures. This compound is used as a basis of a series of analogues with effectively a zero-length linker. Fluorescence properties of all these analogues are described, together with the kinetics of their interaction with rabbit skeletal myosin subfragment 1 in the presence and absence of actin. One particular analogue, deac-aminoATP [3'-(7-diethylaminocoumarin-3-carbonylamino)-3'-deoxyadenosine 5'-triphosphate], shows a 17-fold enhancement of fluorescence upon binding to this (skeletal) myosin II. As the diphosphate, it exhibits a large signal change upon dissociation from the actomyosin, with kinetics similar to those of natural ADP. The ability of this set of analogues to produce large signals indicated potential uses when scarce proteins are studied in small amounts.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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A Series of Related Nucleotide Analogues that Aids Optimization of Fluorescence Signals in Probing the Mechanism of P-Loop ATPases, Such as Actomyosin

Webb¹,

Reid²,

Munasinghe³

et al. 2004

Biochemistry

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“…3-Azido-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-3-deoxy-β-D-ribofuranose, 16, was prepared in seven steps from xylose following a slightly altered literature procedure. 33 Coupling with N 6 -(3-iodobenzyl)adenine by the method of Vorbru ¨ggen et al, 34 followed by alkaline deprotection, yielded 18% of the β-anomer 17. Reduction of the azido moiety with triphenylphosphine led to smooth conversion of 17 to the desired amine 12 without detectable loss of the benzylic N 6 -substituent.…”

Section: Mutant Vs Wildmentioning

confidence: 99%

Neoceptor Concept Based on Molecular Complementarity in GPCRs: A Mutant Adenosine A₃ Receptor with Selectively Enhanced Affinity for Amine-Modified Nucleosides

et al. 2001

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Adenosine A(3) receptors are of interest in the treatment of cardiac ischemia, inflammation, and neurodegenerative diseases. In an effort to create a unique receptor mutant that would be activated by tailor-made synthetic ligands, we mutated the human A(3) receptor at the site of a critical His residue in TM7, previously proposed to be involved in ligand recognition through interaction with the ribose moiety. The H272E mutant receptor displayed reduced affinity for most of the uncharged A(3) receptor agonists and antagonists examined. For example, the nonselective agonist 1a was 19-fold less potent at the mutant receptor than at the wild-type receptor. The introduction of an amino group on the ribose moiety of adenosine resulted in either equipotency or enhanced binding affinity at the H272E mutant relative to wild-type A(3) receptors, depending on the position of the amino group. 3'-Amino-3'-deoxyadenosine proved to be 7-fold more potent at the H272E mutant receptor than at the wild-type receptor, while the corresponding 2'- and 5'-amino analogues did not display significantly enhanced affinities. An 3'-amino-N(6)-iodobenzyl analogue showed only a small enhancement at the mutant (K(i) = 320 nM) vs wild-type receptors. The 3'-amino group was intended for a direct electrostatic interaction with the negatively charged ribose-binding region of the mutant receptor, yet molecular modeling did not support this notion. This design approach is an example of engineering the structure of mutant receptors to recognize synthetic ligands for which they are selectively matched on the basis of molecular complementarity between the mutant receptor and the ligand. We have termed such engineered receptors "neoceptors", since the ligand recognition profile of such mutant receptors need not correspond to the profile of the parent, native receptor.

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ChemInform Abstract: AMINONUCLEOSIDES AND THEIR DERIVATIVES. VI. A NEW SYNTHESIS OF 1,2,5‐TRI‐O‐ACYL‐3‐AZIDO‐3‐DEOXY‐β‐D‐RIBOFURANOSE

Abstract: Aus dem Xylofuranose‐Derivat (I) wird nach Acylierung das Triflat (III) hergestellt, das mit Lithiumazid.

Cited by 2 publications

References 1 publication

A Series of Related Nucleotide Analogues that Aids Optimization of Fluorescence Signals in Probing the Mechanism of P-Loop ATPases, Such as Actomyosin

A Series of Related Nucleotide Analogues that Aids Optimization of Fluorescence Signals in Probing the Mechanism of P-Loop ATPases, Such as Actomyosin

Neoceptor Concept Based on Molecular Complementarity in GPCRs: A Mutant Adenosine A₃ Receptor with Selectively Enhanced Affinity for Amine-Modified Nucleosides

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ChemInform Abstract: AMINONUCLEOSIDES AND THEIR DERIVATIVES. VI. A NEW SYNTHESIS OF 1,2,5‐TRI‐O‐ACYL‐3‐AZIDO‐3‐DEOXY‐β‐D‐RIBOFURANOSE

Abstract: Aus dem Xylofuranose‐Derivat (I) wird nach Acylierung das Triflat (III) hergestellt, das mit Lithiumazid.

Cited by 2 publications

References 1 publication

A Series of Related Nucleotide Analogues that Aids Optimization of Fluorescence Signals in Probing the Mechanism of P-Loop ATPases, Such as Actomyosin

A Series of Related Nucleotide Analogues that Aids Optimization of Fluorescence Signals in Probing the Mechanism of P-Loop ATPases, Such as Actomyosin

Neoceptor Concept Based on Molecular Complementarity in GPCRs: A Mutant Adenosine A3 Receptor with Selectively Enhanced Affinity for Amine-Modified Nucleosides

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Product

Resources

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Neoceptor Concept Based on Molecular Complementarity in GPCRs: A Mutant Adenosine A₃ Receptor with Selectively Enhanced Affinity for Amine-Modified Nucleosides