Himastatin
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| Category | Antibiotics |
| Catalog number | BBF-00963 |
| CAS | 126775-74-4 |
| Molecular Weight | 1485.67 |
| Molecular Formula | C72H104N14O20 |
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Description
Himastatin is a cyclic ester peptide antibiotic produced by Streptomyces hygroscopicus. It has anti-Gram-positive bacteria activity and anti-tumor cell activity.
Specification
| IUPAC Name | (1S,4R,7S,12R,14R,17S,20R,23S,31R)-28-[(1S,4R,7S,12R,14R,17S,20R,23S,31R)-12,31-dihydroxy-20-[(1S)-1-hydroxyethyl]-17-(2-methylpropyl)-2,5,8,15,18,21-hexaoxo-4,7-di(propan-2-yl)-6-oxa-3,9,10,16,19,22,24-heptazapentacyclo[20.10.0.09,14.023,31.025,30]dotriaconta-25(30),26,28-trien-28-yl]-12,31-dihydroxy-20-[(1S)-1-hydroxyethyl]-17-(2-methylpropyl)-4,7-di(propan-2-yl)-6-oxa-3,9,10,16,19,22,24-heptazapentacyclo[20.10.0.09,14.023,31.025,30]dotriaconta-25(30),26,28-triene-2,5,8,15,18,21-hexone |
| Canonical SMILES | CC(C)CC1C(=O)NC(C(=O)N2C(CC3(C2NC4=C3C=C(C=C4)C5=CC6=C(C=C5)NC7C6(CC8N7C(=O)C(NC(=O)C(NC(=O)C9CC(CNN9C(=O)C(OC(=O)C(NC8=O)C(C)C)C(C)C)O)CC(C)C)C(C)O)O)O)C(=O)NC(C(=O)OC(C(=O)N2C(CC(CN2)O)C(=O)N1)C(C)C)C(C)C)C(C)O |
| InChI | InChI=1S/C72H104N14O20/c1-29(2)19-45-57(91)81-53(35(13)87)63(97)83-49(61(95)79-51(31(5)6)67(101)105-55(33(9)10)65(99)85-47(59(93)75-45)23-39(89)27-73-85)25-71(103)41-21-37(15-17-43(41)77-69(71)83)38-16-18-44-42(22-38)72(104)26-50-62(96)80-52(32(7)8)68(102)106-56(34(11)12)66(100)86-48(24-40(90)28-74-86)60(94)76-46(20-30(3)4)58(92)82-54(36(14)88)64(98)84(50)70(72)78-44/h15-18,21-22,29-36,39-40,45-56,69-70,73-74,77-78,87-90,103-104H,19-20,23-28H2,1-14H3,(H,75,93)(H,76,94)(H,79,95)(H,80,96)(H,81,91)(H,82,92)/t35-,36-,39+,40+,45-,46-,47+,48+,49-,50-,51+,52+,53+,54+,55-,56-,69-,70-,71+,72+/m0/s1 |
| InChI Key | OZPNLJQULOIOGU-UPABGHPRSA-N |
Properties
| Appearance | White Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | >200°C(dec.) |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in chloroform, methanol |
Reference Reading
1. Dimerization decrypts antibiotic activity
Myles Smith Science. 2022 Feb 25;375(6583):820-821. doi: 10.1126/science.abn8327. Epub 2022 Feb 24.
Direct dimerization simplifies the synthesis of himastatin and elucidates its mode of action.
2. Enhancement of himastatin bioproduction via inactivation of atypical repressors in Streptomyces hygroscopicus
Yunchang Xie, Qinglian Li, Xiangjing Qin, Jianhua Ju, Junying Ma Metab Eng Commun. 2019 Jan 5;8:e00084. doi: 10.1016/j.mec.2018.e00084. eCollection 2019 Jun.
Three atypical regulatory genes, hmtABD have been discovered within the himastatin biosynthetic gene cluster (BGC) in Streptomyces hygroscopicus ATCC 53653 and the roles of their products have been identified. HmtA and HmtD do not show any structurally distinct features characteristic of regulatory function yet were shown to play important repressive and stimulatory roles, respectively, related to himastatin biosynthesis. HmtB encodes a conserved acetylglutamate kinase; new member of this family serves as repressor of secondary metabolism. Through repressive networks engineering, the limiting functions of HmtA and HmtB along with the activating functions of HmtD in the himastatin BGC have been identified for the first time by gene activation, qPCR, RT-PCR and HPLC studies of selected mutant strains; two of these mutant strains (ΔhmtA and ΔhmtB) produced himastatin in titers (19.02 ± 1.2 μg/mL, 9.9 folds and 30.40 ± 0.83 μg/mL, 15.8 folds) far exceeding those of the wild-type (WT) producer. Overall, this work provides significant insight into secondary metabolic regulatory mechanisms in Streptomyces. These efforts also highlight and validate a new strategy enabling expanded exploitation of cyclopeptidic natural products such as himastatin that demonstrate exciting antimicrobial and antitumor potentials.
3. Total synthesis of himastatin
Kyan A D'Angelo, Carly K Schissel, Bradley L Pentelute, Mohammad Movassaghi Science. 2022 Feb 25;375(6583):894-899. doi: 10.1126/science.abm6509. Epub 2022 Feb 24.
The natural product himastatin has an unusual homodimeric structure that presents a substantial synthetic challenge. We report the concise total synthesis of himastatin from readily accessible precursors, incorporating a final-stage dimerization strategy that was inspired by a detailed consideration of the compound's biogenesis. Combining this approach with a modular synthesis enabled expedient access to more than a dozen designed derivatives of himastatin, including synthetic probes that provide insight into its antibiotic activity.
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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 ╳
