Albonoursin

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

Hodoodo CAT#: H592472

CAS#: 1222-90-8

Description: Albonoursin is an antibacterial cyclic dipeptide.

Chemical Structure

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Albonoursin
CAS# 1222-90-8
Instruction

Theoretical Analysis

Hodoodo Cat#: H592472
Name: Albonoursin
CAS#: 1222-90-8
Chemical Formula: C15H16N2O2
Exact Mass: 256.12
Molecular Weight: 256.305
Elemental Analysis: C, 70.29; H, 6.29; N, 10.93; O, 12.48

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 @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Albonoursin; B-73; P-42-2

IUPAC/Chemical Name: 2,5-Piperazinedione, 3-benzylidene-6-isobutylidene-

InChi Key: LCIIOYPBHIZBOD-QHKWOANTSA-N

InChi Code: InChI=1S/C15H16N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-10H,1-2H3,(H,16,19)(H,17,18)/b12-8+,13-9+

SMILES Code: O=C(/C(NC/1=O)=C\C2=CC=CC=C2)NC1=C\C(C)C

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: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 256.31 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: Li Y, Lai YM, Lu Y, Yang YL, Chen S. Analysis of the biosynthesis of antibacterial cyclic dipeptides in Nocardiopsis alba. Arch Microbiol. 2014 Nov;196(11):765-74. doi: 10.1007/s00203-014-1015-x. Epub 2014 Jul 22. PubMed PMID: 25048158.

2: Gondry M, Sauguet L, Belin P, Thai R, Amouroux R, Tellier C, Tuphile K, Jacquet M, Braud S, Courçon M, Masson C, Dubois S, Lautru S, Lecoq A, Hashimoto S, Genet R, Pernodet JL. Cyclodipeptide synthases are a family of tRNA-dependent peptide bond-forming enzymes. Nat Chem Biol. 2009 Jun;5(6):414-20. doi: 10.1038/nchembio.175. PubMed PMID: 19430487.

3: Kanzaki H, Imura D, Nitoda T, Kawazu K. Enzymatic conversion of cyclic dipeptides to dehydro derivatives that inhibit cell division. J Biosci Bioeng. 2000;90(1):86-9. PubMed PMID: 16232823.

4: Kanzaki H, Yanagisawa S, Nitoda T. Enzymatic synthesis of dehydro cyclo(His-Phe)s, analogs of the potent cell cycle inhibitor, dehydrophenylahistin, and their inhibitory activities toward cell division. Biosci Biotechnol Biochem. 2004 Nov;68(11):2341-5. PubMed PMID: 15564674.

5: Kanzaki H, Yanagisawa S, Kanoh K, Nitoda T. A novel potent cell cycle inhibitor dehydrophenylahistin--enzymatic synthesis and inhibitory activity toward sea urchin embryo. J Antibiot (Tokyo). 2002 Dec;55(12):1042-7. PubMed PMID: 12617513.

6: Lautru S, Gondry M, Genet R, Pernodet JL. The albonoursin gene Cluster of S noursei biosynthesis of diketopiperazine metabolites independent of nonribosomal peptide synthetases. Chem Biol. 2002 Dec;9(12):1355-64. PubMed PMID: 12498889.

7: Gondry M, Lautru S, Fusai G, Meunier G, Ménez A, Genet R. Cyclic dipeptide oxidase from Streptomyces noursei. Isolation, purification and partial characterization of a novel, amino acyl alpha,beta-dehydrogenase. Eur J Biochem. 2001 Mar;268(6):1712-21. PubMed PMID: 11248691.

8: Kanzaki H, Yanagisawa S, Nitoda T. Biosynthetic intermediates of the tetradehydro cyclic dipeptide albonoursin produced by Streptomyces albulus KO-23. J Antibiot (Tokyo). 2000 Nov;53(11):1257-64. PubMed PMID: 11213286.

9: Kanzaki H, Imura D, Nitoda T, Kawazu K. Effective production of dehydro cyclic dipeptide albonoursin exhibiting pronuclear fusion inhibitory activity. II. Biosynthetic and bioconversion studies. J Antibiot (Tokyo). 2000 Jan;53(1):58-62. PubMed PMID: 10724009.

10: Kanzaki H, Imura D, Sashida R, Kobayashi A, Kawazu K. Effective production of dehydro cyclic dipeptide albonoursin exhibiting pronuclear fusion inhibitory activity. I. Taxonomy and fermentation. J Antibiot (Tokyo). 1999 Nov;52(11):1017-22. PubMed PMID: 10656574.

11: Fukushima K, Yazawa K, Arai T. Biological activities of albonoursin. J Antibiot (Tokyo). 1973 Mar;26(3):175-6. PubMed PMID: 4783201.

12: Shin C, Chigira Y, Masaki M, Ota M. Synthesis of albonoursin. Bull Chem Soc Jpn. 1969 Jan;42(1):191-3. PubMed PMID: 5775961.