Ac-5SGlcNAc

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MedKoo CAT#: 466073

CAS#: 67561-97-1

Description: 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

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Ac-5SGlcNAc
CAS# 67561-97-1
Instruction

Theoretical Analysis

MedKoo Cat#: 466073
Name: Ac-5SGlcNAc
CAS#: 67561-97-1
Chemical Formula: C16H23NO9S
Exact Mass: 405.11
Molecular Weight: 405.418
Elemental Analysis: C, 47.40; H, 5.72; N, 3.45; O, 35.52; S, 7.91

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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).

Biological target:
In vitro activity:
In vivo activity:

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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.