CAS 80943-41-5

Methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranoside

Description:

Methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranoside, with CAS number 80943-41-5, is a complex glycoside characterized by its unique structural features. This compound contains a glucopyranoside moiety, which is a six-membered sugar ring, and is modified with a dideoxy sugar component, indicating the absence of hydroxyl groups at specific positions. The presence of a cyclohexene ring with multiple hydroxyl groups contributes to its potential biological activity and solubility properties. The stereochemistry of the molecule is significant, as it includes specific chiral centers that influence its interactions with biological systems. This compound may exhibit properties relevant to medicinal chemistry, particularly in the context of glycosylation reactions or as a potential lead compound in drug development. Its complex structure suggests that it could participate in various biochemical pathways, making it of interest for further research in pharmacology and biochemistry.

Formula: C₁₄H₂₅NO₈

InChI: InChI=1S/C14H25NO8/c1-5-8(11(19)13(21)14(22-2)23-5)15-7-3-6(4-16)9(17)12(20)10(7)18/h3,5,7-21H,4H2,1-2H3/t5-,7+,8-,9-,10+,11+,12+,13-,14+/m1/s1

InChI key: InChIKey=KFHKERRGDZTZQJ-SHCNSHNESA-N

SMILES: N([C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1C)[C@H]2C=C(CO)[C@@H](O)[C@H](O)[C@H]2O

Synonyms:

• (S)-Acarviosin
• Acarviosin
• Acarviosine
• Methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-<span class="text-smallcaps">D</span>-glucopyranoside
• a-D-Glucopyranoside, methyl4,6-dideoxy-4-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-,[1S-(1a,4a,5b,6a)]-
• α-<span class="text-smallcaps">D</span>-Glucopyranoside, methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-
• α-<span class="text-smallcaps">D</span>-Glucopyranoside, methyl 4,6-dideoxy-4-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-, [1S-(1α,4α,5β,6α)]-
• α-D-Glucopyranoside, methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-
• Methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranoside
• α-D-Glucopyranoside, methyl 4,6-dideoxy-4-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-, [1S-(1α,4α,5β,6α)]-
• Methyl 4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-alpha-D-glucopyranoside

Acarviosin

CAS: 80943-41-5

Stability Hygroscopic
Applications Acarviosin is a part of the potent α-amylase inhibitor, Acarbose (A123500), an anti-diabetic drug used to treat type 2 diabetes mellitus (1,2,3).
References (1) Shibata, Y., et al.: Carbohydrate. Res., 228, 377 (1992) (2) Raimbaud, E., et al.: Carbohydrate. Res., 227, 351 (1992) (3) Geng, P., et al.: Carbohydr Res. 343, 882 (2008)https://www.ncbi.nlm.nih.gov/pubmed/18294624PMID: 18294624

Formula: C₁₄H₂₅NO₈

Color and Shape: Neat

Molecular weight: 335.35

Ref: TR-A123550

Acarviosin

CAS: 80943-41-5

Acarviosin is a chemical compound that is structurally related to the antimicrobial peptide Ac-LLL-Nal-OH. It is an antidiabetic agent that has been shown to be effective for the treatment of type 2 diabetes and associated cardiovascular risk factors. Acarviosin was originally isolated from a bacterial strain and has been chemically synthesized for use in the treatment of diabetes. Acarviosin inhibits both glycan synthesis and enzyme activities, leading to reduced levels of glucose in blood plasma. This drug also exhibits pharmacokinetic properties with a half-life of approximately 15 hours, which allows it to be taken once daily. Acarviosin can also be used as an analytical method for identifying disaccharides by cleaving them at the glycosidic bond, releasing monosaccharides as products.

Formula: C₁₄H₂₅NO₈

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 335.35 g/mol

Ref: 3D-OA34981