Name: Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc
Brand: BOC Sciences
Price: 1980 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

1 g

$1980

In stock

Synonyms

β-D-Glucopyranosiduronic acid, 2-[[3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1-oxopropyl]amino]-4-(hydroxymethyl)phenyl, methyl ester, 2,3,4-triacetate; (2S,3S,4S,5R,6S)-methyl-6-(2-(3-(((9H-fluoren-9-yl)methoxy)carbonyl-amino) propanamido)-4-(hydroxymethyl)phenoxy)-3,4,5-triacetoxy-tetrahydro-2H-pyran-2-carboxylate

IUPAC Name

methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]-4-(hydroxymethyl)phenoxy]oxane-2-carboxylate

Canonical SMILES

CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=C(C=C(C=C2)CO)NC(=O)CCNC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)C(=O)OC)OC(=O)C

InChI

InChI=1S/C38H40N2O14/c1-20(42)50-32-33(51-21(2)43)35(52-22(3)44)37(54-34(32)36(46)48-4)53-30-14-13-23(18-41)17-29(30)40-31(45)15-16-39-38(47)49-19-28-26-11-7-5-9-24(26)25-10-6-8-12-27(25)28/h5-14,17,28,32-35,37,41H,15-16,18-19H2,1-4H3,(H,39,47)(H,40,45)/t32-,33-,34-,35+,37+/m0/s1

InChIKey

COFWDBMZXNIYIR-DVEMFWCFSA-N

Solubility

10 mm in DMSO

Shelf Life

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

Shipping

Room temperature

Storage

Store at 2-8 °C

Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc is a specialized cleavable linker that significantly contributes to the functionality and precision of antibody-drug conjugates (ADCs). These linkers are crucial in the targeted delivery of cytotoxic drugs to cancer cells while minimizing the effects on healthy tissues. The molecule's structure includes a glucopyranuronate moiety, which is strategically designed to be responsive to specific enzymatic activities within the tumor microenvironment. This enzymatic cleavability is highly beneficial because it allows for the controlled release of the drug specifically in cancerous cells, where enzymes like beta-glucuronidase are overexpressed, thus enhancing the selectivity and effectiveness of ADCs against tumors.

One of the standout features of Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc is its stability in systemic circulation, paired with its ability to release the drug payload in a controlled manner inside target cells. The inclusion of the triacetyl glucopyranuronate unit ensures that the linker remains intact during its journey through the bloodstream, thereby preventing premature drug release and enhancing overall treatment safety and efficacy. This stable transport mechanism is crucial in improving the therapeutic window of ADCs, allowing higher dosages to reach the tumor cells before the cytotoxic drug is activated and released.

Additionally, the presence of the Fmoc (Fluorenylmethyloxycarbonyl) group in Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc offers versatility during the synthetic process of ADCs. The Fmoc group serves as a protective group that can be easily removed under mild conditions, facilitating the incorporation of various payloads and enabling precise modifications of the ADC structure. This feature is particularly valuable in the laboratory setting, where ease of synthesis and customization are essential for developing diverse ADCs with specific properties tailored to different types of cancer or other diseases requiring targeted treatment.

Furthermore, Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc is instrumental in advancing the field of precision medicine. By providing a mechanism to deliver drugs in a highly targeted manner, it supports the development of personalized therapies that can reduce adverse effects and improve patient outcomes. Researchers can exploit this linker's cleavable nature and protective Fmoc group to design ADCs that better match the biological characteristics of specific tumors, thereby increasing the efficacy of the treatment. The adaptability of this linker allows for the continuous refinement of ADCs, ensuring that they remain at the forefront of innovative cancer therapies. Overall, Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc serves as a critical component in the synthesis of ADCs, enhancing the ability to create sophisticated, targeted treatments that offer hope for improved cancer care.

COA

HNMR

HPLC

Catalog	Product Name	CAS	Inquiry
BADC-00957	Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2	148579-93-5

What is Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc?

Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc is a protected sugar-based linker used in ADC synthesis. The triacetyl protection enhances solubility and stability, while the Fmoc group allows selective deprotection and conjugation to antibodies or other biomolecules.

7/7/2019

Could you kindly explain how Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc supports ADC development?

It serves as a stable and versatile linker that improves solubility and facilitates controlled conjugation reactions. The Fmoc-protected hydroxyl group allows stepwise functionalization, supporting site-specific payload attachment in ADCs.

10/10/2022

We are interested in the storage recommendations for Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc.

Store this compound at -20°C in a dry, inert atmosphere, protected from light. Such conditions maintain the integrity of the Fmoc group and prevent deacetylation or hydrolysis, preserving its reactivity for ADC conjugation.

3/10/2016

Could you kindly advise if certificates and analytical documents are available for Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc?

BOC Sciences provides complete CoA, NMR, and LC-MS documentation verifying molecular identity, structural integrity, and suitability for conjugation, ensuring reproducible results in ADC synthesis.

18/9/2018

Dear team, which analytical methods are recommended for Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc?

NMR spectroscopy, LC-MS, and HPLC are recommended for confirming the structural integrity, Fmoc protection, and triacetyl group stability, enabling quality assurance in ADC linker preparation.

20/2/2019

— Dr. Peter Adams, Medicinal Chemist (UK)

Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc performed exceptionally in our glycosylated ADC synthesis.

3/10/2016

— Ms. Laura Bennett, Biochemist (USA)

High purity and batch consistency of Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc facilitated reproducible reactions.

20/2/2019

— Prof. Emily White, Medicinal Chemist (UK)

Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc was essential for our glycosylation studies. BOC Sciences delivered high-quality product with clear documentation.

18/9/2018

— Prof. Emily White, Medicinal Chemist (UK)

Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc was essential for our glycosylation studies. The product quality and documentation provided by BOC Sciences were outstanding.

7/7/2019

— Mr. Thomas Green, Chemist (Germany)

BOC Sciences provided prompt delivery with detailed QC, ensuring smooth ADC workflow.

— Dr. Elizabeth Hall, Senior Scientist (USA)

Technical guidance helped us integrate Me-triacetyl-β-D-glucopyranuronate-Ph-CH2OH-Fmoc efficiently into multi-step syntheses.

10/10/2022