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Cirramycin A1

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Cirramycin A1
Category Antibiotics
Catalog number BBF-00346
CAS 25339-90-6
Molecular Weight 597.74
Molecular Formula C31H51NO10

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Capabilities & Facilities

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

It is produced by the strain of Streptomyces cirratus 12090. Cirramycin A1 has anti-gram-positive and negative bacterial activity, it is also effective against a variety of mycoplasmas, the minimum inhibitory concentration against mycoplasmas pneumonia is 0.001 μg/mL.

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Synonyms UNII-1CV2O1UP9R; Antibiotic B 58941 B
IUPAC Name 2-[(1S,2R,3R,7R,8S,9S,10R,12R,14E,16S)-9-[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
Canonical SMILES CCC1C(C2C(O2)(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC3C(C(C(C(O3)C)O)N(C)C)O)CC=O)C)C)C
InChI InChI=1S/C31H51NO10/c1-9-23-18(4)29-31(6,42-29)12-10-21(34)16(2)14-20(11-13-33)28(17(3)22(35)15-24(36)40-23)41-30-27(38)25(32(7)8)26(37)19(5)39-30/h10,12-13,16-20,22-23,25-30,35,37-38H,9,11,14-15H2,1-8H3/b12-10+/t16-,17+,18-,19-,20+,22-,23-,25+,26-,27-,28-,29+,30+,31+/m1/s1
InChI Key PYLRKBRNWXMGSG-MDYHIPEWSA-N
Appearance White Acicular Crystalline
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Melting Point 145-148 °C
1. New cirramycin-family antibiotics F-1 and F-2. Selection of producer mutants, fermentation, isolation, structural elucidation and antibacterial activity
Y Sawada, T Tsuno, T Miyaki, T Naito, T Oki J Antibiot (Tokyo). 1989 Feb;42(2):242-53. doi: 10.7164/antibiotics.42.242.
Two new 16-membered macrolides, cirramycins F-1 and F-2, were isolated from the culture filtrate of a mutant strain B-1425 of Streptomyces cirratus JTB-3. The antibiotics were also produced by bio-transformation of cirramycin A1 using a blocked mutant strain A-0033. Structures of F-1 and F-2 have been elucidated by spectral interpretation and analysis of acid degradation products. Both involved isomeric modification of a neutral sugar; F-1 contained L-rhodinose, and F-2 L-amicetose. Based on spectral data, cirramycin F-1 and antibiotic A6888C were found to be identical. Cirramycins F-1 and F-2 are active against Gram-positive bacteria, but less active than cirramycin A1.

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