Tunicamycin D
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| Category | Antibiotics |
| Catalog number | BBF-05928 |
| CAS | 66081-38-7 |
| Molecular Weight | 858.98 |
| Molecular Formula | C40H66N4O16 |
| Purity | ≥95% |
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Description
Tunicamycin D is a member of the tunicamycin group of nucleoside antibiotics, which are known for their antibacterial, antiviral, and antitumor activities. These activities are primarily due to the inhibition of bacterial phospho-N-acetylmuramyl-pentapeptide transferase (MraY), an enzyme crucial for the biosynthesis of peptidoglycan, which is a major component of bacterial cell walls. Tunicamycins also inhibit the human enzyme UDP-N-acetylglucosamine-dolichyl phosphate N-acetylglucosamine-phosphotransferase (GPT), which is involved in the first step of N-linked glycosylation of proteins in the endoplasmic reticulum. This inhibition can lead to the prevention of N-glycan attachment to proteins, affecting their proper folding, trafficking, and function, and ultimately inducing cellular stress and apoptosis.
Specification
| Related CAS | 76544-58-6 (Deleted CAS) 2304869-59-6 (Deleted CAS) |
| Synonyms | 2,4(1H,3H)-Pyrimidinedione, 1-[(11S)-11-O-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl]-6,10-dideoxy-10-[[(2E)-15-methyl-1-oxo-2-hexadecen-1-yl]amino]-L-galacto-β-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl]-; 1-[(11S)-11-O-[2-(Acetylamino)-2-deoxy-α-D-glucopyranosyl]-6,10-dideoxy-10-[[(2E)-15-methyl-1-oxo-2-hexadecen-1-yl]amino]-L-galacto-β-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl]-2,4(1H,3H)-pyrimidinedione; 2,4(1H,3H)-Pyrimidinedione, 1-[(11S)-11-O-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl]-6,10-dideoxy-10-[[(2E)-15-methyl-1-oxo-2-hexadecenyl]amino]-L-galacto-β-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl]-; 2,4(1H,3H)-Pyrimidinedione, 1-[[10(E),11S]-11-O-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl]-6,10-dideoxy-10-[(15-methyl-1-oxo-2-hexadecenyl)amino]-L-galacto-β-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl]-; Corynetoxin U 17i; Tunicamycin D2; Tunicamycin D2 homolog |
| Storage | Store at -20 °C |
| IUPAC Name | (E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-15-methylhexadec-2-enamide |
| Canonical SMILES | O=C1C=CN(C(=O)N1)C2OC(C(O)CC3OC(OC4OC(CO)C(O)C(O)C4NC(=O)C)C(NC(=O)C=CCCCCCCCCCCCC(C)C)C(O)C3O)C(O)C2O |
| InChI | InChI=1S/C40H66N4O16/c1-21(2)15-13-11-9-7-5-4-6-8-10-12-14-16-26(48)42-29-33(53)30(50)24(57-39(29)60-38-28(41-22(3)46)32(52)31(51)25(20-45)58-38)19-23(47)36-34(54)35(55)37(59-36)44-18-17-27(49)43-40(44)56/h14,16-18,21,23-25,28-39,45,47,50-55H,4-13,15,19-20H2,1-3H3,(H,41,46)(H,42,48)(H,43,49,56)/b16-14+/t23-,24-,25-,28-,29-,30+,31-,32-,33-,34+,35-,36-,37-,38-,39+/m1/s1 |
| InChI Key | XCEPHNBEHQJSSB-LGJGITPNSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Density | 1.39±0.1 g/cm3 |
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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
