CAS 132489-69-1

D-Gluconimidic acid, 2-(acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-, δ-lactone, (1Z)-

Description:

D-Gluconimidic acid, 2-(acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-, δ-lactone, with CAS number 132489-69-1, is a complex organic compound characterized by its lactone structure, which is a cyclic ester formed from the reaction of a hydroxyl group and a carboxylic acid. This compound features an acetylamino group, indicating the presence of an acetyl group attached to an amino group, which contributes to its reactivity and potential biological activity. The phenylamino group suggests that it may exhibit aromatic characteristics, potentially influencing its solubility and interaction with biological systems. The presence of the gluconimidic acid moiety indicates that it may be involved in biochemical processes, possibly related to carbohydrate metabolism. Its δ-lactone configuration implies that it may have unique properties in terms of stability and reactivity, making it of interest in medicinal chemistry and drug development. Overall, this compound's structural features suggest potential applications in pharmaceuticals, particularly in the development of glycosylated compounds or enzyme inhibitors.

Formula: C₁₅H₁₉N₃O₇

InChI: InChI=1S/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1

InChI key: InChIKey=PBLNJFVQMUMOJY-JXZOILRNSA-N

SMILES: N(\OC(NC1=CC=CC=C1)=O)=C\2/[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O2

Synonyms:

• <span class="text-smallcaps">D</span>-Gluconimidic acid, 2-(acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-, δ-lactone, (1Z)-
• N-Acetylglucosaminono-1,5-Lactoneo-(Phenylcarbamoyl)Oxime
• N-[(2Z,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(phenylcarbamoyl)oxy]imino}tetrahydro-2H-pyran-3-yl]acetamide (non-preferred name)
• O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate
• acetamidodeoxy-D-glucopyranosylideneamino phenylcarbamate
• D-Gluconimidic acid, 2-(acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-, δ-lactone, (1Z)-

(Z)-PUGNAc

CAS: 132489-69-1

(Z)-PUGNAc

Formula: C₁₅H₁₉N₃O₇

Purity: 98%

Color and Shape: Solid-Crystals

Molecular weight: 353.32726

Ref: 54-BICL4035

(Z)-PUGNAc

CAS: 132489-69-1

(Z)-PUGNAc

Formula: C₁₅H₁₉N₃O₇

Purity: ≥95%

Molecular weight: 353.331

Ref: 54-BUP02905

(5R,6R,7S,8R,Z)-6,7-Dihydroxy-8-(hydroxymethyl)-2,3-dioxo-N-((phenylcarbamoyl)oxy)-1,4-oxazocane-5-carbimidic acid

CAS: 132489-69-1

Formula: C₁₅H₁₇N₃O₉

Purity: 98%

Color and Shape: Solid

Molecular weight: 383.3102

Ref: IN-DA0010QF

(Z)-PUGNAc

CAS: 132489-69-1

(Z)-PUGNAc is a potent O-GlcNAcase inhibitor that is more active than (E)-PUGNAc, removes O-GlcNAc from proteins (peptide O-GlcNAc-β-N-acetylaminoglucosidase),

Formula: C₁₅H₁₉N₃O₇

Purity: 98.72%

Color and Shape: Solid

Molecular weight: 353.3273

Ref: TM-T38722

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate

Controlled Product

CAS: 132489-69-1

Stability Moisture and Temperature Sensitive
Applications An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B.
References Baji, H., et al,: Eur. J. Med. Chem., 30, 617 (1995), Vaaje-Kolstad, G., et al.: J. Biol. Chem., 279, 3612 (2004), Perreira, M., et al.: Bioorg. Med. Chem., 14, 837 (2006).

Formula: C₁₅H₁₉N₃O₇

Color and Shape: Neat

Molecular weight: 353.33

Ref: TR-A157250

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate

CAS: 132489-69-1

Ref: 7W-GC4687

(Z)-PUGNAc

CAS: 132489-69-1

N-((3R,4R,5S,6R,Z)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(((phenylcarbamoyl)oxy)imino)tetrahydro-2H-pyran-3-yl)acetamide

Formula: C₁₅H₁₉N₃O₇

Purity: 98%

Molecular weight: 353.33

Ref: IN-DG01496384

(Z)-PugNAc

CAS: 132489-69-1

PUGNAc (O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate) is a potent inhibitor of O-GlcNAcase, the enzyme that removes O-linked N-acetylglucosamine from intracellular proteins. It increases global O-GlcNAcylation levels by blocking O-GlcNAcase and is widely used to study the biological effects of altered O-linked protein glycosylation. PUGNAc also inhibits the related lysosomal enzyme β-hexosaminidase, which is mainly of interest in research to understand lysosomal function, glycoconjugate metabolism, or the role of hexosaminidases in pathogens, such as bacteria and parasites that use similar enzymes to process sugars.

Formula: C₁₅H₁₉N₃O₇

Purity: Min. 97 Area-%

Color and Shape: White Powder

Molecular weight: 353.33 g/mol

Ref: 3D-EA06838

PUGNAc extrapure, 95%

CAS: 132489-69-1

Formula: C₁₅H₁₉N₃O₇

Molecular weight: 353.33

Ref: SR-59750