Kistamicin A
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| Category | Antibiotics |
| Catalog number | BBF-01548 |
| CAS | 155683-50-4 |
| Molecular Weight | 1171.55 |
| Molecular Formula | C61H51ClN8O15 |
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Description
Kistamicin A is produced by the strain of Microtetraspora parvasata subsp. kistna. It has antiviral effect, and its ID50 (μg/mL) against influenza virus MDCK cells and herpes simplex virus are respectively 3.6 and 44. It also has anti-gram-positive bacterial effects.
Specification
| Synonyms | Kistamycin A |
| IUPAC Name | (1S,22R,25R,28R,31R,42R)-22-[[(2R)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-34-chloro-25-(3,5-dihydroxyphenyl)-38,51-dihydroxy-23,26,29,44,46-pentaoxo-7,36-dioxa-18,24,27,30,43,45-hexazanonacyclo[29.13.2.23,6.232,35.18,12.113,17.137,41.010,28.016,20]tripentaconta-3(53),4,6(52),8,10,12(51),13(50),14,16,19,32,34,37,39,41(47),48-hexadecaene-42-carboxylic acid |
| Canonical SMILES | C1C2C(=O)NC(C3=CC(=C(C=C3)O)OC4=C(C=C(C=C4)C(C(=O)N2)NC(=O)C5C6=CC(=C(C(=C6)OC7=CC=C1C=C7)O)C8=CC9=C(C=C8)C(=CN9)CC(C(=O)NC(C(=O)N5)C1=CC(=CC(=C1)O)O)NC(=O)C(CC1=CC=C(C=C1)O)N)Cl)C(=O)O |
| InChI | InChI=1S/C61H51ClN8O15/c62-41-20-30-7-14-47(41)85-48-23-31(6-13-46(48)74)53(61(82)83)70-56(77)44-16-28-3-10-38(11-4-28)84-49-24-33-19-40(54(49)75)29-5-12-39-34(26-64-43(39)21-29)22-45(65-55(76)42(63)15-27-1-8-35(71)9-2-27)57(78)67-51(32-17-36(72)25-37(73)18-32)59(80)69-52(33)60(81)68-50(30)58(79)66-44/h1-14,17-21,23-26,42,44-45,50-53,64,71-75H,15-16,22,63H2,(H,65,76)(H,66,79)(H,67,78)(H,68,81)(H,69,80)(H,70,77)(H,82,83)/t42-,44+,45-,50-,51-,52-,53-/m1/s1 |
| InChI Key | UFHMIPMOTWJTKL-GSGYMRTMSA-N |
Properties
| Appearance | Pale Yellow Powder |
| Antibiotic Activity Spectrum | viruses; Gram-positive bacteria |
| Melting Point | >300°C |
| Density | 1.67±0.1 g/cm3 |
Reference Reading
1. Kistamicin biosynthesis reveals the biosynthetic requirements for production of highly crosslinked glycopeptide antibiotics
Anja Greule, Thierry Izoré, Dumitrita Iftime, et al. Nat Commun. 2019 Jun 13;10(1):2613. doi: 10.1038/s41467-019-10384-w.
Kistamicin is a divergent member of the glycopeptide antibiotics, a structurally complex class of important, clinically relevant antibiotics often used as the last resort against resistant bacteria. The extensively crosslinked structure of these antibiotics that is essential for their activity makes their chemical synthesis highly challenging and limits their production to bacterial fermentation. Kistamicin contains three crosslinks, including an unusual 15-membered A-O-B ring, despite the presence of only two Cytochrome P450 Oxy enzymes thought to catalyse formation of such crosslinks within the biosynthetic gene cluster. In this study, we characterise the kistamicin cyclisation pathway, showing that the two Oxy enzymes are responsible for these crosslinks within kistamicin and that they function through interactions with the X-domain, unique to glycopeptide antibiotic biosynthesis. We also show that the kistamicin OxyC enzyme is a promiscuous biocatalyst, able to install multiple crosslinks into peptides containing phenolic amino acids.
2. Complete Genome Sequence of Actinomadura Parvosata Subsp. Kistnae, A Rich Source of Novel Natural Product (Bio-)Chemistry
Kalina Kusserow, Tobias A M Gulder J Genomics. 2017 Jul 2;5:75-76. doi: 10.7150/jgen.19673. eCollection 2017.
The soil dwelling actinomycete strain Actinomadura parvosata subsp. kistnae is the producer of the antiviral antibiotics kistamicin A and B. Genome sequencing and bioinformatic analysis revealed the presence of the kistamycin biosynthetic gene cluster responsible for the formation of these non-ribosomal peptides as well as an impressive number of yet uncharacterized biosynthetic pathways. This includes polyketide, ribosomal and non-ribosomal peptide and a large number of terpenoid biosynthetic loci encoding yet unknown natural products. The genomic data of this strain is thus a treasure trove for genome mining for novel functional metabolites and new biocatalysts.
3. New antiviral antibiotics, kistamicins A and B. II. Structure determination
N Naruse, M Oka, M Konishi, T Oki J Antibiot (Tokyo). 1993 Dec;46(12):1812-8. doi: 10.7164/antibiotics.46.1812.
The structures of antiviral antibiotics kistamicins A and B have been determined by a combination of chemical degradation and spectral analysis. They are commonly composed of D-tyrosine, 3,5-dihydrophenylglycine, a biphenyl ether bis-amino acid, and a diphenyl substituted indole tris-amino acid, forming a tricyclic ring structure. Kistamicin B possessed a phenethylamide at the amino terminal of kistamicin A. They are structurally related to the nuclei of the vancomycin group antibiotics particularly to antibiotic complestatin.
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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 ╳
