Allosamidin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571271

CAS#: 103782-08-7

Description: Allosamidin is a chitinase inhibitor and typical secondary metabolite of Streptomyces. It may be used as a pesticide and anti-asthmatic agent.

Chemical Structure

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Allosamidin
CAS# 103782-08-7
Instruction

Theoretical Analysis

MedKoo Cat#: 571271
Name: Allosamidin
CAS#: 103782-08-7
Chemical Formula: C25H42N4O14
Exact Mass: 622.27
Molecular Weight: 622.630
Elemental Analysis: C, 48.23; H, 6.80; N, 9.00; O, 35.97

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Allosamidin; A 82516; A-82516; A82516

IUPAC/Chemical Name: N-((2R,3R,4S,5S,6R)-5-(((2S,3R,4S,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-(((3aR,4R,5R,6R,6aS)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]oxazol-5-yl)oxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

InChi Key: MDWNFWDBQGOKNZ-ZRBHDKNQSA-N

InChi Code: InChI=1S/C25H42N4O14/c1-8(33)26-14-17(36)16(35)11(6-31)39-23(14)42-22-12(7-32)40-24(15(19(22)38)27-9(2)34)41-21-10(5-30)20-13(18(21)37)28-25(43-20)29(3)4/h10-24,30-32,35-38H,5-7H2,1-4H3,(H,26,33)(H,27,34)/t10-,11-,12-,13-,14-,15-,16-,17+,18-,19+,20+,21-,22-,23+,24+/m1/s1

SMILES Code: CN(C)C1=N[C@@H]2[C@H]([C@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](CO)O4)O)O)NC(C)=O)[C@@H](O)[C@H]3NC(C)=O)[C@@H]([C@@H]2O1)CO)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 622.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Suzuki S, Nagasawa H, Sakuda S. Identification of the allosamidin-releasing factor in allosamidin-producing Streptomyces. J Antibiot (Tokyo). 2014 Feb;67(2):195-7. doi: 10.1038/ja.2013.109. Epub 2013 Oct 30. PubMed PMID: 24169800.

2: Sato Y, Suzuki S, Muraoka S, Kikuchi N, Noda N, Matsumoto T, Inoue H, Nagasawa H, Sakuda S. Preparation of allosamidin and demethylallosamidin photoaffinity probes and analysis of allosamidin-binding proteins in asthmatic mice. Bioorg Med Chem. 2011 May 15;19(10):3054-9. doi: 10.1016/j.bmc.2011.04.012. Epub 2011 Apr 13. PubMed PMID: 21530272.

3: Suzuki S, Nakanishi E, Ohira T, Kawachi R, Nagasawa H, Sakuda S. Chitinase inhibitor allosamidin is a signal molecule for chitinase production in its producing Streptomyces I. Analysis of the chitinase whose production is promoted by allosamidin and growth accelerating activity of allosamidin. J Antibiot (Tokyo). 2006 Jul;59(7):402-9. PubMed PMID: 17025016.

4: Wang Y, Liu T, Yang Q, Li Z, Qian X. A modeling study for structure features of β-N-acetyl-D-hexosaminidase from Ostrinia furnacalis and its novel inhibitor allosamidin: species selectivity and multi-target characteristics. Chem Biol Drug Des. 2012 Apr;79(4):572-82. doi: 10.1111/j.1747-0285.2011.01301.x. Epub 2012 Jan 30. PubMed PMID: 22177554.

5: Huang G. Recent progress on synthesis and activities of allosamidin and its analogues. Mini Rev Med Chem. 2012 Jun;12(7):665-70. Review. PubMed PMID: 22512553.

6: Suzuki S, Nakanishi E, Ohira T, Kawachi R, Ohnishi Y, Horinouchi S, Nagasawa H, Sakuda S. Chitinase inhibitor allosamidin is a signal molecule for chitinase production in its producing Streptomyces II. Mechanism for regulation of chitinase production by allosamidin through a two-component regulatory system. J Antibiot (Tokyo). 2006 Jul;59(7):410-7. PubMed PMID: 17025017.

7: Suzuki S, Nakanishi E, Furihata K, Miyamoto K, Tsujibo H, Watanabe T, Ohnishi Y, Horinouchi S, Nagasawa H, Sakuda S. Chitinase inhibitor allosamidin promotes chitinase production of Streptomyces generally. Int J Biol Macromol. 2008 Jul 1;43(1):13-9. Epub 2007 Sep 29. PubMed PMID: 17977593.

8: Vaaje-Kolstad G, Houston DR, Rao FV, Peter MG, Synstad B, van Aalten DM, Eijsink VG. Structure of the D142N mutant of the family 18 chitinase ChiB from Serratia marcescens and its complex with allosamidin. Biochim Biophys Acta. 2004 Jan 14;1696(1):103-11. PubMed PMID: 14726210.

9: Baban J, Fjeld S, Sakuda S, Eijsink VG, Sørlie M. The roles of three Serratia marcescens chitinases in chitin conversion are reflected in different thermodynamic signatures of allosamidin binding. J Phys Chem B. 2010 May 13;114(18):6144-9. doi: 10.1021/jp909801x. PubMed PMID: 20397673.

10: Rao FV, Houston DR, Boot RG, Aerts JM, Sakuda S, van Aalten DM. Crystal structures of allosamidin derivatives in complex with human macrophage chitinase. J Biol Chem. 2003 May 30;278(22):20110-6. Epub 2003 Mar 14. PubMed PMID: 12639956.

11: Matsuura H, Okamoto S, Anamnart S, Wang Q, Zhou ZY, Nihira T, Yamada Y, Kuzuyama T, Seto H, Nakayama J, Suzuki A, Nagasawa H, Sakuda S. Nucleotide sequences of genes encoding allosamidin-sensitive and -insensitive chitinases produced by allosamidin-producing Streptomyces. Biosci Biotechnol Biochem. 2003 Sep;67(9):2002-5. PubMed PMID: 14519991.

12: Milewski S, O'Donnell RW, Gooday GW. Chemical modification studies of the active centre of Candida albicans chitinase and its inhibition by allosamidin. J Gen Microbiol. 1992 Dec;138(12):2545-50. PubMed PMID: 1362581.

13: Cederkvist FH, Saua SF, Karlsen V, Sakuda S, Eijsink VG, Sørlie M. Thermodynamic analysis of allosamidin binding to a family 18 chitinase. Biochemistry. 2007 Oct 30;46(43):12347-54. Epub 2007 Oct 4. PubMed PMID: 17915946.

14: Cho JY, Rosenthal P, Miller M, Pham A, Aceves S, Sakuda S, Broide DH. Targeting AMCase reduces esophageal eosinophilic inflammation and remodeling in a mouse model of egg induced eosinophilic esophagitis. Int Immunopharmacol. 2014 Jan;18(1):35-42. doi: 10.1016/j.intimp.2013.10.026. Epub 2013 Nov 13. PubMed PMID: 24239745; PubMed Central PMCID: PMC3908829.

15: Takenaka Y, Nakano S, Tamoi M, Sakuda S, Fukamizo T. Chitinase gene expression in response to environmental stresses in Arabidopsis thaliana: chitinase inhibitor allosamidin enhances stress tolerance. Biosci Biotechnol Biochem. 2009 May;73(5):1066-71. Epub 2009 May 7. PubMed PMID: 19420714.

16: Papanikolau Y, Tavlas G, Vorgias CE, Petratos K. De novo purification scheme and crystallization conditions yield high-resolution structures of chitinase A and its complex with the inhibitor allosamidin. Acta Crystallogr D Biol Crystallogr. 2003 Feb;59(Pt 2):400-3. Epub 2003 Jan 23. PubMed PMID: 12554965.

17: Sándor E, Pusztahelyi T, Karaffa L, Karányi Z, Pócsi I, Biró S, Szentirmai A, Pócsi I. Allosamidin inhibits the fragmentation of Acremonium chrysogenum but does not influence the cephalosporin-C production of the fungus. FEMS Microbiol Lett. 1998 Jul 15;164(2):231-6. PubMed PMID: 9742010.

18: Villagómez-Castro JC, Calvo-Méndez C, López-Romero E. Chitinase activity in encysting Entamoeba invadens and its inhibition by allosamidin. Mol Biochem Parasitol. 1992 May;52(1):53-62. PubMed PMID: 1625707.

19: Andronopoulou E, Vorgias CE. Purification and characterization of a new hyperthermostable, allosamidin-insensitive and denaturation-resistant chitinase from the hyperthermophilic archaeon Thermococcus chitonophagus. Extremophiles. 2003 Feb;7(1):43-53. Epub 2002 Oct 18. PubMed PMID: 12579379.

20: Germer A, Klod S, Peter MG, Kleinpeter E. NMR spectroscopic and theoretical study of the complexation of the inhibitor allosamidin in the binding pocket of the plant chitinase hevamine. J Mol Model. 2002 Aug;8(8):231-6. PubMed PMID: 12324799.