Zelkovamycin
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| Category | Antibiotics |
| Catalog number | BBF-03475 |
| CAS | 221197-33-7 |
| Molecular Weight | 779.86 |
| Molecular Formula | C36H45N9O9S |
| Purity | ≥95% |
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Description
It is a cyclic peptide antibiotic produced by the strain of Streptomyces sp. K96-0670. It has anti-Xanthomonas oryzae, Acholeplasma laidlawii, Piricularia oryzae and Staphylococcus aureus activity, but no effect on other bacteria and fungi.
Specification
| Synonyms | Cyclo[2-aminobutanoyl-(2Z)-2-amino-2-butenoyl-N-methylglycyl-2-(1-aminoethyl)-4-thiazolecarbonyl-7-methoxytryptophyl-3-oxoisovalylglycyl]; Zelcovamycin |
| IUPAC Name | (16Z)-7-acetyl-13-ethyl-16-ethylidene-4-[(7-methoxy-1H-indol-3-yl)methyl]-7,18,22-trimethyl-24-thia-3,6,9,12,15,18,21,26-octazabicyclo[21.2.1]hexacosa-1(25),23(26)-diene-2,5,8,11,14,17,20-heptone |
| Canonical SMILES | CCC1C(=O)NC(=CC)C(=O)N(CC(=O)NC(C2=NC(=CS2)C(=O)NC(C(=O)NC(C(=O)NCC(=O)N1)(C)C(=O)C)CC3=CNC4=C3C=CC=C4OC)C)C |
| InChI | InChI=1S/C36H45N9O9S/c1-8-22-30(49)41-23(9-2)34(52)45(6)16-28(48)39-18(3)33-43-25(17-55-33)31(50)42-24(13-20-14-37-29-21(20)11-10-12-26(29)54-7)32(51)44-36(5,19(4)46)35(53)38-15-27(47)40-22/h9-12,14,17-18,22,24,37H,8,13,15-16H2,1-7H3,(H,38,53)(H,39,48)(H,40,47)(H,41,49)(H,42,50)(H,44,51)/b23-9- |
| InChI Key | VYMRECQGDKKGCJ-AQHIEDMUSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycoplasma |
| Boiling Point | 1291.5±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Zelkovamycin, a new cyclic peptide antibiotic from Streptomyces sp. K96-0670. I. Production, isolation and biological properties
N Tabata, M Shinose, M Oohori, H Tomoda, S Omura, H Zhang, Y Takahashi J Antibiot (Tokyo) . 1999 Jan;52(1):29-33. doi: 10.7164/antibiotics.52.29.
A new antibiotic termed zelkovamycin was isolated from the fermentation broth of Streptomyces sp. K96-0670 by solvent extraction, ODS column chromatography and preparative HPLC. Zelkovamycin showed antibacterial activity against Xanthomonas oryzae, Acholeplasma laidlawii, Pyricularia oryzae and Staphylococcus aureus.
2. Zelkovamycin, a new cyclic peptide antibiotic from Streptomyces sp. K96-0670. II. Structure elucidation
H Zhang, R Uchida, H Tomoda, S Omura, N Tabata J Antibiot (Tokyo) . 1999 Jan;52(1):34-9. doi: 10.7164/antibiotics.52.34.
The structure of antibiotic zelkovamycin was elucidated as a cyclic peptide comprising glycyl, 2-aminobutanoyl, 2-amino-2-butenoyl, N-methyl glycyl, alanyl, 1,3-thiazoyl, 7-methoxytryptophanyl and 2-methyldehydrothreonyl residues. The sequence of the amino acids was established by spectroscopic studies including 1H-1H COSY, 13C-1H COSY, 13C-1H HMQC, 13C-1H HMBC, 15N-1H HMQC and 15N-1H HMBC NMR experiments.
3. Zelkovamycins B-E, Cyclic Octapeptides Containing Rare Amino Acid Residues from an Endophytic Kitasatospora sp
Shan Cen, Yuqin Zhang, Liyan Yu, Maoluo Gan, Xiaomeng Hao, Yufeng Liu, Rebecca J M Goss, Jack A Connolly, Yujia Wang, Jiaqing Yu Org Lett . 2020 Dec 4;22(23):9346-9350. doi: 10.1021/acs.orglett.0c03565.
Four unusual cyclopeptides, zelkovamycins B-E (1-4), were isolated from an endophyticKitasatosporasp. Zelkovamycin B was featured by an unprecedented 3-methyl-5-hydroxypyrrolidine-2,4-dione ring system linked to the cyclopeptide skeleton. Their structures and full configurations were established by spectroscopic analysis, Marfey's method, and NMR calculations. A plausible biosynthetic pathway for zelkovamycins was proposed based on gene cluster analysis. Zelkovamycin E displayed potent inhibitory activity against H1N1 influenza A virus.
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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 ╳
