Aspartocin D

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Aspartocin D
Category Antibiotics
Catalog number BBF-04212
CAS 1562369-96-3
Molecular Weight 1262.37
Molecular Formula C56H87N13O20
Purity ≥95% by HPLC

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Description

Aspartocin D is a minor analogue of the amphomycin complex, a family of lipopeptide antibiotic produced by Streptomyces canus. Aspartocin D has the activity against Gram-positive bacteria with MIC of 0.125 μg/ml for B. subtilis and is presumed to act by inhibiting bacterial cell wall peptidoglycan synthesis, however its bioprofile and potential utility has not been extensively investigated. The antibacterial activity is calcium-dependent, with MICs ranging from 0.06-4 and 0.25-8 μg/ml for B. subtilis and S. aureus, respectively, in the presence of higher (2.5 mM) to lower (0.125 mM) calcium concentrations.

Specification

Synonyms N-[(3Z)-9-methyl-1-oxo-3-decen-1-yl]-L-alpha-aspartyl-(2S,3R)-2,3-diaminobutanoyl-(2R)-2-piperidinecarbonyl-(3S)-3-methyl-L-alpha-aspartyl-L-alpha-aspartylglycyl-L-alpha-aspartylglycyl-(2R,3R)-2,3-diaminobutanoyl-L-valyl-L-proline(11→2)-lactam
Storage Store at -20°C
IUPAC Name (3S)-4-[[(3S,4R,7S,13S,16R,22S,28S,34R)-16-[(1R)-1-aminoethyl]-31-[(1S)-1-carboxyethyl]-22,28-bis(carboxymethyl)-4-methyl-2,6,12,15,18,21,24,27,30,33-decaoxo-13-propan-2-yl-1,5,11,14,17,20,23,26,29,32-decazatricyclo[32.4.0.07,11]octatriacontan-3-yl]amino]-3-[[(Z)-9-methyldec-3-enoyl]amino]-4-oxobutanoic acid
Canonical SMILES CC1C(C(=O)N2CCCCC2C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N3CCCC3C(=O)N1)C(C)C)C(C)N)CC(=O)O)CC(=O)O)C(C)C(=O)O)NC(=O)C(CC(=O)O)NC(=O)CC=CCCCCC(C)C
InChI InChI=1S/C56H87N13O20/c1-27(2)16-11-9-8-10-12-19-37(70)61-34(24-42(77)78)49(81)67-46-31(7)60-50(82)36-18-15-21-69(36)54(86)43(28(3)4)65-53(85)45(30(6)57)64-39(72)26-59-47(79)32(22-40(73)74)62-38(71)25-58-48(80)33(23-41(75)76)63-52(84)44(29(5)56(88)89)66-51(83)35-17-13-14-20-68(35)55(46)87/h10,12,27-36,43-46H,8-9,11,13-26,57H2,1-7H3,(H,58,80)(H,59,79)(H,60,82)(H,61,70)(H,62,71)(H,63,84)(H,64,72)(H,65,85)(H,66,83)(H,67,81)(H,73,74)(H,75,76)(H,77,78)(H,88,89)/b12-10-/t29-,30+,31+,32-,33-,34-,35+,36
InChI Key RWKODFJGLUVNKT-IJVAMUGQSA-N

Properties

Appearance Off-white to Fawn Solid
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 1699.0±65.0°C at 760 mmHg
Density 1.4±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO

Reference Reading

1. Two novel amphomycin analogues from Streptomyces canus strain FIM-0916
Kai Huang, Wei Zheng, Huang-Jian Yang, Jian Zhou, Zhu-Lan Zhang, Xiao-Zhen Huang, Chuan-Xi Wang, Jing-Ming Zhou Nat Prod Res . 2014;28(12):861-7. doi: 10.1080/14786419.2014.886210.
Three lipopeptides, the known compound amphomycin, together with two novel compounds named aspartocin D (1) and aspartocin E (2) were obtained from the fermentation broth extraction of Streptomyces canus strain FIM0916 by using various column chromatography techniques. Their structures were elucidated by using spectroscopic methods, mainly by an extensive NMR analysis. It was demonstrated that compounds 1 and 2 are novel analogues of amphomycin, whose structures are similar to aspartocins. Compounds 1 and 2 share the same cyclic decapeptide core of cyclo (Dab2-Pip3-MeAsp4-Asp5-Gly6-Asp7-Gly8-Dab9-Val10-Pro11-), differing only in the side-chain moiety corresponding to Asp1-△3-isohendecenoic acid and Asp1-△3-isododecenoic acid, for aspartocin D and aspartocin E. In bioassays, compounds 1 and 2 exhibited antimicrobial activities against Gram-positive bacteria in the presence of Ca(2+) (1.25 mM); particularly, the activities were enhanced with higher concentrations of calcium.

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