Pyralomicin 2a

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Category Antibiotics
Catalog number BBF-02090
CAS 139636-00-3
Molecular Weight 460.26
Molecular Formula C19H19Cl2NO8

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Description

Pyralomicin 2a is an antibiotic produced by Actinomadura spiralis MI 178-34F18. Antibacterial activity.

Specification

IUPAC Name 2,6-dichloro-1-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-5-hydroxy-8-methylchromeno[2,3-b]pyrrol-4-one
Canonical SMILES CC1=CC(=C(C2=C1OC3=C(C2=O)C=C(N3C4C(C(C(C(O4)CO)OC)O)O)Cl)O)Cl
InChI InChI=1S/C19H19Cl2NO8/c1-6-3-8(20)13(25)11-12(24)7-4-10(21)22(18(7)30-16(6)11)19-15(27)14(26)17(28-2)9(5-23)29-19/h3-4,9,14-15,17,19,23,25-27H,5H2,1-2H3/t9-,14-,15-,17-,19-/m1/s1
InChI Key ZXYNPGZWOMFXHV-JUTSKPLTSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum bacteria
Boiling Point 745.2±60.0°C at 760 mmHg
Melting Point 295-297°C (dec.)
Density 1.8±0.1 g/cm3

Reference Reading

1. Pyralomicins, novel antibiotics from Microtetraspora spiralis. II. Structure determination
N Kawamura, R Sawa, Y Takahashi, K Isshiki, T Sawa, H Naganawa, T Takeuchi J Antibiot (Tokyo). 1996 Jul;49(7):651-6. doi: 10.7164/antibiotics.49.651.
Novel antibiotics, pyralomicins 1a approximately 1d, 2a approximately 2c were isolated from the culture broth of Microtetraspora spiralis MI178-34F18. The structures of pyralomicins were determined by various NMR spectral analyses including 1H-15N HMBC and 13C¿1H¿ NOE difference experiments.
2. Pyralomicins, novel antibiotics from Microtetraspora spiralis. IV. Absolute configuration
N Kawamura, H Nakamura, R Sawa, Y Takahashi, T Sawa, H Naganawa, T Takeuchi J Antibiot (Tokyo). 1997 Feb;50(2):147-9. doi: 10.7164/antibiotics.50.147.
The absolute configurations of pyralomicin la and pyralomicin 2a were determined by X-ray crystallographic analyses of crystalline 7'-O-p-bromobenzoylpyralomicin 1a and 2'-O-p-bromobenzoylpyralomicin 2a derived from pyralomicin 1a and pyralomicin 2a using anomalous scattering of the bromine atom. The absolute configurations of pyralomicins 1b approximately 1d and 2b approximately 2e were suggested to be the same as pyralomicin 1a and pyralomicin 2a, respectively, by comparing the circular dichroism spectra.

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