Sisomicin B
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| Category | Antibiotics |
| Catalog number | BBF-02992 |
| CAS | 53797-16-3 |
| Molecular Weight | 433.50 |
| Molecular Formula | C18H35N5O7 |
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Description
It is an aminoglycoside antibiotic produced by the strain of Micromonospora inyoensis. It has broad-spectrum antimicrobial activity.
Specification
| Synonyms | Sisomicin B; 6-O-[3-Deoxy-3-(methylamino)-α-D-xylopyranosyl]-4-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hexa-4-enopyranosyl)-2-deoxy-D-streptamine; Antibiotic 66-40B; 6640B; D-Streptamine, O-3-deoxy-3-(methylamino)-alpha-D-xylopyranosyl-(1-6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy- |
| IUPAC Name | (2R,3R,4S,5S)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-4-(methylamino)oxane-3,5-diol |
| Canonical SMILES | CNC1C(COC(C1O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O |
| InChI | InChI=1S/C18H35N5O7/c1-23-12-11(24)6-27-18(13(12)25)30-16-10(22)4-9(21)15(14(16)26)29-17-8(20)3-2-7(5-19)28-17/h2,8-18,23-26H,3-6,19-22H2,1H3/t8-,9+,10-,11-,12+,13-,14+,15-,16+,17-,18-/m1/s1 |
| InChI Key | DAKDDLIZULPEFW-WXGYIBDGSA-N |
Properties
| Appearance | Amorphous Powder |
| Boiling Point | 682.7±55.0°C at 760 mmHg |
| Melting Point | 91-102°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Use of a glycomics array to establish the anti-carbohydrate antibody repertoire in type 1 diabetes
Paul M H Tran, Fran Dong, Eileen Kim, Katherine P Richardson, Lynn K H Tran, Kathleen Waugh, Diane Hopkins, Richard D Cummings, Peng George Wang, Marian J Rewers, Jin-Xiong She, Sharad Purohit Nat Commun. 2022 Nov 1;13(1):6527. doi: 10.1038/s41467-022-34341-2.
Type 1 diabetes (T1D) is an autoimmune disease, characterized by the presence of autoantibodies to protein and non-protein antigens. Here we report the identification of specific anti-carbohydrate antibodies (ACAs) that are associated with pathogenesis and progression to T1D. We compare circulatory levels of ACAs against 202 glycans in a cross-sectional cohort of T1D patients (n = 278) and healthy controls (n = 298), as well as in a longitudinal cohort (n = 112). We identify 11 clusters of ACAs associated with glycan function class. Clusters enriched for aminoglycosides, blood group A and B antigens, glycolipids, ganglio-series, and O-linked glycans are associated with progression to T1D. ACAs against gentamicin and its related structures, G418 and sisomicin, are also associated with islet autoimmunity. ACAs improve discrimination of T1D status of individuals over a model with only clinical variables and are potential biomarkers for T1D.
2. Individual p K a Values of Tobramycin, Kanamycin B, Amikacin, Sisomicin, and Netilmicin Determined by Multinuclear NMR Spectroscopy
Abdulaziz H Alkhzem, Timothy J Woodman, Ian S Blagbrough ACS Omega. 2020 Aug 11;5(33):21094-21103. doi: 10.1021/acsomega.0c02744. eCollection 2020 Aug 25.
NMR spectroscopy is a powerful technique for separating and measuring each distinct pK a value of the amino groups around aminoglycoside antibiotics. Unambiguous assignments were made for each individual amine substituent on 2-deoxystreptamine, tobramycin, kanamycin B, amikacin, sisomicin, and netilmicin using variations in the NMR spectroscopic chemical shift (δ) with 1H, 13C, and 15N HMBC; the individual pK a values of netilmicin are reported for the first time.
3. Advances in novel antibiotics to treat multidrug-resistant gram-negative bacterial infections
Aaron Matlock, Joshua Allan Garcia, Kayvan Moussavi, Brit Long, Stephen Yuan-Tung Liang Intern Emerg Med. 2021 Nov;16(8):2231-2241. doi: 10.1007/s11739-021-02749-1. Epub 2021 May 6.
Antimicrobial resistance is a growing threat to public health and an increasingly common problem for acute care physicians to confront. Several novel antibiotics have been approved in the past decade to combat these infections; however, physicians may be unfamiliar with how to appropriately utilize them. The purpose of this review is to evaluate novel antibiotics active against resistant gram-negative bacteria and highlight clinical information regarding their use in the acute care setting. This review focuses on novel antibiotics useful in the treatment of infections caused by resistant gram-negative organisms that may be seen in the acute care setting. These novel antibiotics include ceftolozane/tazobactam, ceftazidime/avibactam, meropenem/vaborbactam, imipenem/cilistatin/relebactam, cefiderocol, plazomicin, eravacycline, and omadacycline. Acute care physicians should be familiar with these novel antibiotics so they can utilize them appropriately.
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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 ╳
