Siderochelin A

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Category Antibiotics
Catalog number BBF-02910
CAS 77550-87-9
Molecular Weight 235.24
Molecular Formula C11H13N3O3

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Description

It is produced by the strain of Nocardia sp. SC 113, Act. sp. 69-209B-89. It has the effect against aerobic and anaerobic bacteria, and has anti-Gram-positive bacteria, Gram-negative bacteria and fungal effects but no anti-Candida albicans effect. The antibacterial activity of Siderochelin A is weaker than iron chelating agent Apoferrosamine. Fe2+, Fe3+, CO2+ and Zn2+ have antagonistic effects on Siderochelin A.

Specification

Synonyms 2H-Pyrrole-2-carboxamide, 3,4-dihydro-4-hydroxy-5-(3-hydroxy-2-pyridinyl)-4-methyl-, (2S,4R)-; 2H-Pyrrole-2-carboxamide, 3,4-dihydro-4-hydroxy-5-(3-hydroxy-2-pyridinyl)-4-methyl-, (2S-trans)-; Antibiotic EM 4940A
IUPAC Name (2S,4R)-4-hydroxy-5-(3-hydroxypyridin-2-yl)-4-methyl-2,3-dihydropyrrole-2-carboxamide
Canonical SMILES CC1(CC(N=C1C2=C(C=CC=N2)O)C(=O)N)O
InChI InChI=1S/C11H13N3O3/c1-11(17)5-6(10(12)16)14-9(11)8-7(15)3-2-4-13-8/h2-4,6,15,17H,5H2,1H3,(H2,12,16)/t6-,11+/m0/s1
InChI Key LKXKFHREZIJJTA-UPONEAKYSA-N

Properties

Appearance Little Flaky Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Fungi
Boiling Point 545.9°C at 760 mmHg
Melting Point 165-168°C
Density 1.51 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Siderochelins with anti-mycobacterial activity from Amycolatopsis sp. LZ149
Chun-Hua Lu, Fang-Wen Ye, Yue-Mao Shen Chin J Nat Med. 2015 Jan;13(1):69-72. doi: 10.1016/S1875-5364(15)60009-7.
Three new compounds, namely siderochelins D (2), E (3), and F (4), together with one known siderochelin A (1), were isolated from Amycolatopsis sp. LZ149 and elucidated by spectroscopic analyses including1D- and 2D-NMR and X-ray single crystal diffraction. Compounds 1-3 showed antibacterial activity against Mycobacterium smegmatis.
2. Siderochelin, a new ferrous-ion chelating agent produced by Nocardia
W C Liu, S M Fisher, J S Wells Jr, C S Ricca, P A Principe, W H Trejo, D P Bonner, J Z Gougoutos, B K Toeplitz, R B Sykes J Antibiot (Tokyo). 1981 Jul;34(7):791-9. doi: 10.7164/antibiotics.34.791.
A new ferrous-ion chelating agent, siderochelin, was isolated from fermentation broths of Nocardia sp. SC 11,340. Siderochelin was produced by conventional submerged culture and purified by solvent extraction and recrystallization. The antibiotic was crystallized from acetonitrile as a mixture of diastereoisomers. The molecular formula of siderochelin was determined as C11H13N3O3 on the basis of elemental analysis and mass spectrometry, and the structure was elucidated by X-ray crystallography. The compound shows a broad spectrum of antimicrobial activity, being active against bacteria, fungi and protozoa.

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