Ac-5SGlcNAc | CAS#67561-97-1 | OGT inhibitor

MedKoo Cat#: 466073 | Name: Ac-5SGlcNAc

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ac-5SGlcNAc is a novel, cell-permeable, potent O-GlcNAc transferase (OGT) inhibitor. Ac-5SGlcNAc can be salvaged by cells and processed via the HBP to generate UDP-5SGlcNAc, which acts as an inhibitor of OGT and leads to decreases in cellular O-GlcNAc levels. Ac-5SGlcNAc acts in cells to decrease global O-GlcNAc levels in a dose and time dependent manner. Ac-5SGlcNAc dramatically decreases O-GlcNAc levels on all proteins, even on proteins such as nup62 that are constitutively and heavily O-GlcNAc modified in cells.

Chemical Structure

Ac-5SGlcNAc

CAS#67561-97-1

Theoretical Analysis

MedKoo Cat#: 466073

Name: Ac-5SGlcNAc

CAS#: 67561-97-1

Chemical Formula: C16H23NO9S

Exact Mass: 405.1094

Molecular Weight: 405.42

Elemental Analysis: C, 47.40; H, 5.72; N, 3.45; O, 35.52; S, 7.91

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Ac-5SGlcNAc; Ac5SGlcNAc; Ac 5SGlcNAc; Ac4-5S-GlcNAc; Ac45S-GlcNAc; Ac4 5S-GlcNAc; Ac4-5SGlcNAc; Ac4-5S GlcNAc; Ac45SGlcNAc; Ac4 5S GlcNAc;

IUPAC/Chemical Name

(2S,3R,4R,5S,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-thiopyran-2,4,5-triyl triacetate

InChi Key

JPEDACNJLBHRPS-QCODTGAPSA-N

InChi Code

InChI=1S/C16H23NO9S/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16+/m1/s1

SMILES Code

O=C(OC[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](NC(C)=O)[C@@H](OC(C)=O)S1)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Glycosyltransferases (GTs) are ubiquitous enzymes that catalyze the assembly of glycoconjugates found throughout all kingdoms of nature. A longstanding problem is the rational design of probes that can be used to manipulate GT activity in cells and tissues. Here we describe the rational design and synthesis of a nucleotide sugar analogue that inhibits, with high potency both in vitro and in cells, the human GT responsible for the reversible post-translational modification of nucleocytoplasmic proteins with O-linked N-acetylglucosamine residues (O-GlcNAc).

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 405.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Olivier-Van Stichelen S, Drougat L, Dehennaut V, El Yazidi-Belkoura I, Guinez C, Mir AM, Michalski JC, Vercoutter-Edouart AS, Lefebvre T. Serum-stimulated cell cycle entry promotes ncOGT synthesis required for cyclin D expression. Oncogenesis. 2012 Dec 10;1(12):e36. doi: 10.1038/oncsis.2012.36. PMID: 23552487; PMCID: PMC3545199. 2. Gloster TM, Zandberg WF, Heinonen JE, Shen DL, Deng L, Vocadlo DJ. Hijacking a biosynthetic pathway yields a glycosyltransferase inhibitor within cells. Nat Chem Biol. 2011 Mar;7(3):174-81. doi: 10.1038/nchembio.520. Epub 2011 Jan 23. PMID: 21258330; PMCID: PMC3202988.