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A-19009

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Category Antibiotics
Catalog number BBF-03129
CAS 87768-72-7
Molecular Weight 272.26
Molecular Formula C10H16N4O5

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

A-19009 is a peptide antibiotic produced by Streptomyces collinus A-19009. It mainly has antifungal and vaginal trichomonas activity.

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Synonyms Antibiotic A 19009; N-(N(3)-Fumaramoyl-2,3-diaminopropanoyl)alanine; L-Alanine, N-L-alanyl-3-((4-amino-1,4-dioxo-2-butenyl)amino)-, (E)-
IUPAC Name (2S)-3-[[(E)-4-amino-4-oxobut-2-enoyl]amino]-2-[[(2S)-2-aminopropanoyl]amino]propanoic acid
Canonical SMILES CC(C(=O)NC(CNC(=O)C=CC(=O)N)C(=O)O)N
InChI InChI=1S/C10H16N4O5/c1-5(11)9(17)14-6(10(18)19)4-13-8(16)3-2-7(12)15/h2-3,5-6H,4,11H2,1H3,(H2,12,15)(H,13,16)(H,14,17)(H,18,19)/b3-2+/t5-,6-/m0/s1
InChI Key GDQNPKRTTCRUSH-KXQHVCLCSA-N
Appearance Colorless Needle Crystal
Antibiotic Activity Spectrum fungi; parasites
Boiling Point 749°C at 760 mmHg
Melting Point 275-280°C
Density 1.368 g/cm3
1. Antibiotic A 19009. Structural investigation and synthesis
J L van der Baan, J W Barnick, F Bickelhaupt J Antibiot (Tokyo). 1983 Jul;36(7):784-92. doi: 10.7164/antibiotics.36.784.
The structure of fermentation product A 19009 was reinvestigated by 13C and 1H NMR spectroscopy and established by independent synthesis to be N2-L-alanyl-N3-fumaramoyl-L-2,3-diaminopropanoic acid (2), i.e. a structure isomeric with the originally proposed structure 1. In contrast to 1 which also was synthesized, 2 has a very low activity against Trichomonas vaginalis.
2. Isolation of CB-25-I, an antifungal antibiotic, from Serratia plymuthica
J Shoji, H Hinoo, R Sakazaki, T Kato, T Hattori, K Matsumoto, K Tawara, J Kikuchi, Y Terui J Antibiot (Tokyo). 1989 Jun;42(6):869-74. doi: 10.7164/antibiotics.42.869.
A new antifungal antibiotic, CB-25-I, was isolated from the culture broth of a strain of Serratia plymuthica. The antibiotic, a water-soluble dipeptide, is structurally related to Sch 37137 and A 19009, both produced by strains of Actinomycetales. The antibiotic exhibits inhibitory activity against Candida albicans in YNB medium (a synthetic medium), but the activity is significantly reduced in Sabouroud dextrose medium.
3. Sch 37137, a novel antifungal compound produced by a Micromonospora sp. Taxonomy, fermentation, isolation, structure and biological properties
R Cooper, A C Horan, F Gentile, V Gullo, D Loebenberg, J Marquez, M Patel, M S Puar, I Truumees J Antibiot (Tokyo). 1988 Jan;41(1):13-9. doi: 10.7164/antibiotics.41.13.
A new antifungal compound, Sch 37137, was isolated from the cultured broth of a Micromonospora sp., SCC 1792. Sch 37137 is structurally related to A 19009, a dipeptide previously discovered from a Streptomyces sp. The compound was weakly active against species of Candida and dermatophytes (mean MICs greater than or equal to 128 micrograms/ml) in Sabouraud dextrose, yeast-nitrogen and modified Eagles minimum essential media; however activity against Candida sp. (mean MICs greater than or equal to 12 micrograms/ml) and dermatophytes (mean MICs greater than or equal to 0.8 microgram/ml) significantly improved in MA medium.

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