Kijanimicin
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| Category | Antibiotics |
| Catalog number | BBF-01894 |
| CAS | 78798-08-0 |
| Molecular Weight | 1317.51 |
| Molecular Formula | C67H100N2O24 |
| Purity | >99% by HPLC |
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Description
A tetronic acid related to saccharocarcin, chlorothricin, versipelostatin and tetrocarcin; contains an unusual nitroaminoglycoside; a potent antibacterial, antimalarial and antitumour active; inhibits transcription from the promoter of GRP78, a gene that is activated as part of a stress signalling pathway under glucose deprivation resulting in unfolded protein response (UPR).
Specification
| Synonyms | NSC 329515; Sch 25663 |
| Storage | -20°C |
| IUPAC Name | methyl N-[(2R,3R,4S,6R)-6-[[(1S,3R,6S,7E,9S,11E,13S,16S,17S,18S,20S,21R,22S,23E)-17-[(2R,4R,5S,6S)-4-[(2S,6S)-4-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-[(2R,4R,5R,6S)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-23-hydroxy-4-(hydroxymethyl)-3,8,12,18,20,22-hexamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-2,4-dimethyl-4-nitrooxan-3-yl]carbamate |
| Canonical SMILES | CC1CC(C(C2C1C3(C(C=C2)C(=CCC(C(=CC4C=C(C(CC45C(=O)C(=C3O)C(=O)O5)C)CO)C)OC6CC(C(C(O6)C)NC(=O)OC)(C)[N+](=O)[O-])C)C)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC)O)OC1CC(C(C(O1)C)O)O)C |
| InChI | InChI=1S/C67H100N2O24/c1-29-15-18-45(88-52-27-65(11,69(79)80)60(38(10)87-52)68-64(78)82-14)30(2)20-40-21-39(28-70)33(5)26-67(40)62(76)53(63(77)93-67)61(75)66(12)42(29)17-16-41-54(66)31(3)19-32(4)57(41)91-51-24-46(56(74)35(7)84-51)89-50-25-47(90-48-22-43(71)55(73)34(6)83-48)59(37(9)86-50)92-49-23-44(72)58(81-13)36(8)85-49/h15-17,20-21,31-38,40-52,54-60,70-75H,18-19,22-28H2,1-14H3,(H,68,78)/b29-15+,30-20+,61-53+/t31-,32-,33+,34-,35-,36-,37-,38+,40+,41-,42-,43-,44+,45-,46+,47?,48-,49+,50-,51-,52-,54+,55-,56-,57-,58-,59?,60-,65-,66+,67-/m0/s1 |
| InChI Key | LKSBZILVASNBPF-HOBFKSJSSA-N |
| Source | Actrinomadura sp. |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor); parasites |
| Density | 1.35 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Synthesis of the α-Linked Digitoxose Trisaccharide Fragment of Kijanimicin: An Unexpected Application of Glycosyl Sulfonates
J Colin Mizia, Clay S Bennett, Mohammed U Syed Org Lett . 2022 Jan 21;24(2):731-735. doi: 10.1021/acs.orglett.1c04190.
Previously, we demonstrated that glycosyl tosylates are effective for the synthesis of β-glycosides of gluco-configured 2-deoxy sugars. Here, we show the same sulfonate system can be used for the selective synthesis of α-glycosides containing the allo-configured 2-deoxy sugar digitoxose. As with previous work, optimal selectivity is obtained through matching the donor with the appropriate arylsulfonyl chloride promoter. The utility of this method is demonstrated through the synthesis of the α-linked digitoxose trisaccharide fragment of kijanimicin.
2. Active site architecture of a sugar N-oxygenase
Nathan A Bruender, James B Thoden, Hazel M Holden, Alex L Zimmer, Megan C Branch Biochemistry . 2013 May 14;52(19):3191-3. doi: 10.1021/bi400407x.
KijD3 is a flavin-dependent N-oxygenase implicated in the formation of the nitro-containing sugar d-kijanose, found attached to the antibiotic kijanimicin. For this investigation, the structure of KijD3 in complex with FMN and its dTDP-sugar substrate was solved to 2.1 Å resolution. In contrast to the apoenzyme structure, the C-terminus of the protein becomes ordered and projects into the active site cleft [Bruender, N. A., Thoden, J. B., and Holden, H. M. (2010) Biochemistry 49, 3517-3524]. The amino group of the dTDP-aminosugar that is oxidized is located 4.9 Å from C4a of the flavin ring. The model provides a molecular basis for understanding the manner in which KijD3 catalyzes its unusual chemical transformation.
3. Spirotetronate polyketides as leads in drug discovery
Emmanuel A Theodorakis, Michelle H Lacoske J Nat Prod . 2015 Mar 27;78(3):562-75. doi: 10.1021/np500757w.
The discovery of chlorothricin (1) defined a new family of microbial metabolites with potent antitumor antibiotic properties collectively referred to as spirotetronate polyketides. These microbial metabolites are structurally distinguished by the presence of a spirotetronate motif embedded within a macrocyclic core. Glycosylation at the periphery of this core contributes to the structural complexity and bioactivity of this motif. The spirotetronate family displays impressive chemical structures, potent bioactivities, and significant pharmacological potential. This review groups the family members based on structural and biosynthetic considerations and summarizes synthetic and biological studies that aim to elucidate their mode of action and explore their pharmacological potential.
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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 ╳
