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Nagstatin

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Nagstatin
Names

IUPAC name 2-[(5R,6S,7R,8S)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-3-yl]acetic acid^[1]
Identifiers
CAS Number	126844-81-3^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL596543
ChemSpider	78442903 115763
PubChem CID	10266740
InChI InChI=1S/C12H17N3O6/c1-5(17)14-9-11(21)10(20)7(4-16)15-6(2-8(18)19)3-13-12(9)15/h3,7,9-11,16,20-21H,2,4H2,1H3,(H,14,17)(H,18,19)/t7-,9-,10+,11-/m1/s1 Key: OBMORLCFLUTVPI-CZULRBLNSA-N^[2]
SMILES CC(=O)N[C@@H]1[C@H]([C@H]([C@H](N2C1=NC(=C2)CC(=O)O)CO)O)O
Properties
Chemical formula	C₁₂H₁₇N₃O₆
Molar mass	299.283 g·mol⁻¹
Melting point	190-195 °C^[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nagstatin is a strong competitive inhibitor of the N-acetyl-β-d-glucosaminidase with the molecular formula C₁₂H₁₇N₃O₆.^[4]^[1]^[5] Nagstatin is produced by the bacterium Streptomyces amakusaensis.^[5]^[6]

References[edit]

^ ^a ^b "Nagstatine". Pubchem.ncbi.NLM.nih.gov.

^ "Nagstatin | CAS#126844-81-3 | inhibitor | MedKoo". medkoo.com.

^ Fugmann, Burkhard (14 May 2014). RÖMPP Lexikon Naturstoffe, 1. Auflage, 1997 (in German). Georg Thieme Verlag. p. 423. ISBN 978-3-13-179291-4.

^ Rauter, Amelia Pilar; Lindhorst, Thisbe (18 June 2013). Carbohydrate Chemistry: Chemical and Biological Approaches Volume 39. Royal Society of Chemistry. p. 110. ISBN 978-1-84973-587-2.

^ ^a ^b Aoyagi, Takaaki; Suda, Hiroyuki; Uotani, Kazumichi; Kojima, Fukiko; Aoyama, Takayuki; Horiguchi, Kayo; Hamada, Masa; Takeuchi, Tomio (1992). "Nagstatin, a new inhibitor of N-acetyl-.BETA.-D-glucosaminidase, produced by Streptomyces amakusaensis MG846-fF3. Taxonomy, production, isolation, physico-chemical properties and biological activities". The Journal of Antibiotics. 45 (9): 1404–1408. doi:10.7164/antibiotics.45.1404. PMID 1429224.

^ Progress in Medicinal Chemistry. Elsevier. 9 February 2011. p. 162. ISBN 978-0-12-381291-9.

Further reading[edit]

Aoyama, Takayuki; Naganawa, Hiroshi; Suda, Hiroyuki; Uotan, Kazumichi; Aoyagi, Takaaki; Takeuchi, Tomio (1992). "The structure of nagstatin, a new inhibitor of N-acetyl-.BETA.-D-glucosaminidase". The Journal of Antibiotics. 45 (9): 1557–1558. doi:10.7164/antibiotics.45.1557. PMID 1429245.

Abdulmalek, Emilia (2007). Synthesis of Nagstatin and Its Analogues. University of Oxford.

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