Chemical Synthesis of the Second Messenger Nicotinic Acid Adenine Dinucleotide Phosphate by Total Synthesis of Nicotinamide Adenine Dinucleotide Phosphate

Dowden, James; Moreau, Christelle; Brown, Richard S.; Berridge, G.; Galione, Antony; Potter, Barry V. L.

doi:10.1002/ange.200460054

Cited by 3 publications

(2 citation statements)

References 24 publications

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“…Although approaches to the chemical synthesis of NAADP and its derivatives have been developed,40 the process of producing NAADP derivatives synthetically is still lengthy and relatively difficult. Chemoenzymatic syntheses of NAD, NADP, and NAADP derivatives have been effectively used to produce novel pyridine dinucleotides since the discovery of the NAD glycohydrolase catalyzed base exchange reaction in the 1950s.…”

Section: Discussionmentioning

confidence: 99%

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release

et al. 2010

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Analogs of nicotinic acid adenine dinucleotide phosphate (NAADP) with substitution at either the 4-or the 5-position position of the nicotinic acid moiety have been synthesized from NADP enzymatically using Aplysia californica ADP-ribosyl cyclase or mammalian NAD glycohydrolase. Substitution at the 4-position of the nicotinic acid resulted in the loss of agonist potency for release of Ca 2+ -ions from sea urchin egg homogenates and in potency for competition ligand binding assays using [ 32 P]NAADP. In contrast, several 5-substituted NAADP derivatives showed high potency for binding and full agonist activity for Ca 2+ release. 5-Azido-NAADP was shown to release calcium from sea urchin egg homogenates at low concentration and to compete with [ 32 P]NAADP in a competition ligand binding assay with an IC 50 of 18 nM, indicating that this compound might be a potential photoprobe useful for specific labeling and identification of the NAADP receptor.

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Section: Discussionmentioning

confidence: 99%

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release

et al. 2010

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“…35,36 Illustrated in Figure 1, the enzyme catalyzed base-exchange reaction was instrumental in producing the substituted NAADP derivatives which were used in this study. In the presence of NADP (or an 8-substituted NADP), and a high concentration of 5-substituted nicotinic acid ( R 1 ), the Aplysia ADP-ribosyl cyclase catalyzes the base exchange of nicotinamide for the 5-substituted nicotinic acid.…”

Section: Resultsmentioning

confidence: 99%

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Substituted on the Nicotinic Acid and Adenine Ribosides. Effects on ReceptorMediated Ca²⁺ Release

et al. 2015

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Nicotinic acid adenine dinucleotide phosphate (NAADP) is a Ca2+ releasing intracellular second messenger in both mammals and echinoderms. We report that large functionalized substituents introduced at the nicotinic acid 5-position are recognized by the sea urchin receptor, albeit with a 20–500 fold loss in agonist potency. 5-(3-Azidopropyl)-NAADP was shown to release Ca2+ with an EC50 of 31 µM and to compete with NAADP for receptor binding with an IC50 of 56 nM. Attachment of charged groups to the nicotinic acid of NAADP is associated with loss of activity, suggesting that the nicotinate riboside moiety is recognized as a neutral zwitterion. Substituents (Br- and N3-) can be introduced at the 8-adenosyl position of NAADP while preserving high potency and agonist efficacy and an NAADP derivative substituted at both the 5-position of the nicotinic acid and at the 8-adenosyl position was also recognized although the agonist potency was significantly reduced.

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Facile chemoenzymatic synthesis of a novel stable mimic of NAD⁺

et al. 2018

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Chemical Synthesis of the Second Messenger Nicotinic Acid Adenine Dinucleotide Phosphate by Total Synthesis of Nicotinamide Adenine Dinucleotide Phosphate

Cited by 3 publications

References 24 publications

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Substituted on the Nicotinic Acid and Adenine Ribosides. Effects on ReceptorMediated Ca²⁺ Release

Facile chemoenzymatic synthesis of a novel stable mimic of NAD⁺

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Chemical Synthesis of the Second Messenger Nicotinic Acid Adenine Dinucleotide Phosphate by Total Synthesis of Nicotinamide Adenine Dinucleotide Phosphate

Cited by 3 publications

References 24 publications

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca2+ Release

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca2+ Release

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Substituted on the Nicotinic Acid and Adenine Ribosides. Effects on ReceptorMediated Ca2+ Release

Facile chemoenzymatic synthesis of a novel stable mimic of NAD+

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Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release

Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Substituted on the Nicotinic Acid and Adenine Ribosides. Effects on ReceptorMediated Ca²⁺ Release

Facile chemoenzymatic synthesis of a novel stable mimic of NAD⁺