Glycocinnasperimicin D
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| Category | Antibiotics |
| Catalog number | BBF-01267 |
| CAS | 99260-73-8 |
| Molecular Weight | 694.78 |
| Molecular Formula | C30H50N10O9 |
| Purity | 95% |
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Description
It is produced by the strain of Nocardia sp. MG615-7F6. It is a glycoside cinnamyl imide histamine antibiotic. It has the activity of anti-gram positive bacteria and negative bacteria. It inhibits leukemia L1210 cell with IC50 of 2.0 μg/mL.
Specification
| Synonyms | Glycocinnaspermicidin D; 2-Propenamide, N-(3-((4-aminobutyl)amino)propyl)-3-(4-((4-((((2-((aminocarbonyl)amino)-2-deoxy-beta-D-xylopyranosyl)amino)carbonyl)amino)-2-((aminoiminomethyl)amino)-2,4,6-trideoxy-alpha-D-glucopyranosyl)oxy)phenyl)-, (E)- |
| IUPAC Name | (E)-N-[3-(4-aminobutylamino)propyl]-3-[4-[5-[[3-(carbamoylamino)-4,5-dihydroxyoxan-2-yl]carbamoylamino]-3-(diaminomethylideneamino)-4-hydroxy-6-methyloxan-2-yl]oxyphenyl]prop-2-enamide |
| Canonical SMILES | CC1C(C(C(C(O1)OC2=CC=C(C=C2)C=CC(=O)NCCCNCCCCN)N=C(N)N)O)NC(=O)NC3C(C(C(CO3)O)O)NC(=O)N |
| InChI | InChI=1S/C30H50N10O9/c1-16-21(39-30(46)40-26-22(38-29(34)45)24(43)19(41)15-47-26)25(44)23(37-28(32)33)27(48-16)49-18-8-5-17(6-9-18)7-10-20(42)36-14-4-13-35-12-3-2-11-31/h5-10,16,19,21-27,35,41,43-44H,2-4,11-15,31H2,1H3,(H,36,42)(H4,32,33,37)(H3,34,38,45)(H2,39,40,46)/b10-7+ |
| InChI Key | RUNVIIGXALSBTN-JXMROGBWSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor) |
| Melting Point | >300 °C (dec.) |
| Density | 1.55 g/cm3 |
| Solubility | Freely soluble in Water |
Reference Reading
1. Glycocinnasperimicin D, a new member of glycocinnamolyspermidine antibiotic
K Dobashi, K Nagaoka, Y Watanabe, M Nishida, M Hamada, H Naganawa, T Takita, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1985 Sep;38(9):1166-70. doi: 10.7164/antibiotics.38.1166.
Glycocinnasperimicin D was isolated from the fermentation filtrate of a strain of Nocardia sp. using various procedures of column chromatography. Glycocinnasperimicin D exhibited broad antibacterial spectrum. Its chemical structure was determined by NMR spectrometric analyses.
2. Synthesis of glycocinnasperimicin D
Taihei Nishiyama, Yoshifumi Kusumoto, Ken Okumura, Kanako Hara, Shohei Kusaba, Keiko Hirata, Yukihiro Kamiya, Minoru Isobe, Keiji Nakano, Hiyoshizo Kotsuki, Yoshiyasu Ichikawa Chemistry. 2010 Jan 11;16(2):600-10. doi: 10.1002/chem.200901745.
The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three-component coupling strategy. The key steps involve the Heck-Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar 9. Glycosyl isocyanate 8 was prepared by the oxidation of isonitrile 10, which displayed excellent reactivity in the coupling event. Synthetic roadblocks, encountered during this synthetic effort, have led to the development of the alpha-selective, Lewis acid catalyzed phenyl glycosylation process with 2-amino-hexopyranose and a procedure for acetonide deprotection without affecting the silyl ethers.
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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 ╳
