Epivaliolamine
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-00846 |
| CAS | |
| Molecular Weight | 209.20 |
| Molecular Formula | C7H15NO6 |
Online Inquiry
Description
Epivaliolamine is a pseudo-aminosugars produced by Streptomyces hygroscopicus sub sp. limoneue. It has a very weak inhibitory substance α-Glucosidase activity.
Specification
| IUPAC Name | (1S,2S,3S,4R,5S,6R)-6-amino-2-(hydroxymethyl)cyclohexane-1,2,3,4,5-pentol |
| Canonical SMILES | C(C1(C(C(C(C(C1O)O)O)N)O)O)O |
| InChI | InChI=1S/C7H15NO6/c8-2-3(10)4(11)6(13)7(14,1-9)5(2)12/h2-6,9-14H,1,8H2/t2-,3+,4-,5+,6+,7+/m1/s1 |
| InChI Key | BNZLTGPXBJPTEK-QVFHJDLNSA-N |
Properties
| Appearance | Powder |
Reference Reading
1. Novel inhibitory effect of N-(2-hydroxycyclohexyl)valiolamine on melanin production in a human skin model
Bum-Ho Bin, Yung Hyup Joo, Ai-Young Lee, Song Seok Shin, Eun-Gyung Cho, Tae Ryong Lee Int J Mol Sci. 2014 Jul 9;15(7):12188-95. doi: 10.3390/ijms150712188.
Hyper-pigmentation causes skin darkness and medical disorders, such as post-inflammatory melanoderma and melasma. Therefore, the development of anti-melanogenic agents is important for treating these conditions and for cosmetic production. In our previous paper, we demonstrated that the anti-diabetic drug voglibose, a valiolamine derivative, is a potent anti-melanogenic agent. In addition, we proposed an alternative screening strategy to identify valiolamine derivatives with high skin permeability that act as anti-melanogenic agents when applied topically. In this study, we synthesized several valiolamine derivatives with enhanced lipophilicity and examined their inhibitory effects in a human skin model. N-(2-hydroxycyclohexyl)valiolamine (HV) possesses a stronger inhibitory effect on melanin production than voglibose in a human skin model, suggesting that HV is a more potent anti-melanogenic agent for the skin.
2. N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity
Sharanbasappa S Karade, Michelle L Hill, J L Kiappes, Rajkumar Manne, Balakishan Aakula, Nicole Zitzmann, Kelly L Warfield, Anthony M Treston, Roy A Mariuzza J Med Chem. 2021 Dec 23;64(24):18010-18024. doi: 10.1021/acs.jmedchem.1c01377. Epub 2021 Dec 6.
Most enveloped viruses rely on the host cell endoplasmic reticulum (ER) quality control (QC) machinery for proper folding of glycoproteins. The key ER α-glucosidases (α-Glu) I and II of the ERQC machinery are attractive targets for developing broad-spectrum antivirals. Iminosugars based on deoxynojirimycin have been extensively studied as ER α-glucosidase inhibitors; however, other glycomimetic compounds are less established. Accordingly, we synthesized a series of N-substituted derivatives of valiolamine, the iminosugar scaffold of type 2 diabetes drug voglibose. To understand the basis for up to 100,000-fold improved inhibitory potency, we determined high-resolution crystal structures of mouse ER α-GluII in complex with valiolamine and 10 derivatives. The structures revealed extensive interactions with all four α-GluII subsites. We further showed that N-substituted valiolamines were active against dengue virus and SARS-CoV-2 in vitro. This study introduces valiolamine-based inhibitors of the ERQC machinery as candidates for developing potential broad-spectrum therapeutics against the existing and emerging viruses.
3. Structure-Based Design of Potent Iminosugar Inhibitors of Endoplasmic Reticulum α-Glucosidase I with Anti-SARS-CoV-2 Activity
Sharanbasappa S Karade, Evelyn J Franco, Ana C Rojas, Kaley C Hanrahan, Alexander Kolesnikov, Wenbo Yu, Alexander D MacKerell Jr, Daniel C Hill, David J Weber, Ashley N Brown, Anthony M Treston, Roy A Mariuzza J Med Chem. 2023 Feb 23;66(4):2744-2760. doi: 10.1021/acs.jmedchem.2c01750. Epub 2023 Feb 10.
Enveloped viruses depend on the host endoplasmic reticulum (ER) quality control (QC) machinery for proper glycoprotein folding. The endoplasmic reticulum quality control (ERQC) enzyme α-glucosidase I (α-GluI) is an attractive target for developing broad-spectrum antivirals. We synthesized 28 inhibitors designed to interact with all four subsites of the α-GluI active site. These inhibitors are derivatives of the iminosugars 1-deoxynojirimycin (1-DNJ) and valiolamine. Crystal structures of ER α-GluI bound to 25 1-DNJ and three valiolamine derivatives revealed the basis for inhibitory potency. We established the structure-activity relationship (SAR) and used the Site Identification by Ligand Competitive Saturation (SILCS) method to develop a model for predicting α-GluI inhibition. We screened the compounds against SARS-CoV-2 in vitro to identify those with greater antiviral activity than the benchmark α-glucosidase inhibitor UV-4. These host-targeting compounds are candidates for investigation in animal models of SARS-CoV-2 and for testing against other viruses that rely on ERQC for correct glycoprotein folding.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
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 ╳
