Antibiotic 67-121C
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| Category | Antibiotics |
| Catalog number | BBF-02998 |
| CAS | 57515-50-1 |
| Molecular Weight | 1291.47 |
| Molecular Formula | C65H98N2O24 |
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Description
It is a heptaene macrolide antibiotic produced by the strain of Actinoplanes caeruleus. It has anti-fungal and yeast activity.
Specification
| Synonyms | 67-121 C; Perimycin A, 21-O-(3-amino-3,6-dideoxy-4-O-beta-D-mannopyranosyl-beta-D-mannopyranosyl)-18-carboxy-21-O-de(4-amino-4,6-dideoxy-D-mannopyranosyl)-18-demethyl-13-deoxo-13-hydroxy-, cyclic 15,19-hemiacetal |
| IUPAC Name | (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4R,5S,6R)-4-amino-3-hydroxy-6-methyl-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1,3,5,7,9,11,13,37-octahydroxy-17-[5-hydroxy-7-[4-(methylamino)phenyl]-7-oxoheptan-2-yl]-18-methyl-15-oxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid |
| Canonical SMILES | CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CC(CC(CC(CC(CC(=O)OC1C(C)CCC(CC(=O)C3=CC=C(C=C3)NC)O)O)O)O)O)O)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)OC5C(C(C(C(O5)CO)O)O)O)N)O |
| InChI | InChI=1S/C65H98N2O24/c1-36-17-15-13-11-9-7-5-6-8-10-12-14-16-18-48(87-63-57(80)55(66)61(38(3)86-63)90-64-59(82)58(81)56(79)52(35-68)88-64)32-51-54(62(83)84)50(77)34-65(85,91-51)33-47(75)29-45(73)27-43(71)25-42(70)26-44(72)28-46(74)31-53(78)89-60(36)37(2)19-24-41(69)30-49(76)39-20-22-40(67-4)23-21-39/h5-18,20-23,36-38,41-48,50-52,54-61,63-64,67-75,77,79-82,85H,19,24-35,66H2,1-4H3,(H,83,84)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+ |
| InChI Key | FZQYJNCKADYOTN-QVDADOJXSA-N |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Fungi; Yeast |
| Boiling Point | 1403.6°C at 760 mmHg |
| Melting Point | 175-180°C (dec.) |
| Density | 1.39 g/cm3 |
| Solubility | Soluble in DMF |
Reference Reading
1. Engineered biosynthesis and characterisation of disaccharide-modified 8-deoxyamphoteronolides
Simon Walmsley, Eimear De Poire, Bernard Rawlings, Patrick Caffrey Appl Microbiol Biotechnol. 2017 Mar;101(5):1899-1905. doi: 10.1007/s00253-016-7986-6. Epub 2016 Nov 17.
Several polyene macrolides are potent antifungal agents that have severe side effects. Increased glycosylation of these compounds can improve water solubility and reduce toxicity. Three extending glycosyltransferases are known to add hexoses to the mycosaminyl sugar residues of polyenes. The Actinoplanes caeruleus PegA enzyme catalyses attachment of a D-mannosyl residue in a β-1,4 linkage to the mycosamine of the aromatic heptaene 67-121A to form 67-121C. NppY from Pseudonocardia autotrophica adds an N-acetyl-D-glucosamine to the mycosamine of 10-deoxynystatin. NypY from Pseudonocardia sp. P1 adds an extra hexose to a nystatin, but the identity of the sugar is unknown. Here, we express the nypY gene in Streptomyces nodosus amphL and show that NypY modifies 8-deoxyamphotericins more efficiently than C-8 hydroxylated forms. The modified heptaene was purified and shown to be mannosyl-8-deoxyamphotericin B. This had the same antifungal activity as amphotericin B but was slightly less haemolytic. Chemical modification of this new disaccharide polyene could give better antifungal antibiotics.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
