Ac4GlcNAlk

Name: Ac4GlcNAlk
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1361993-37-4

Cat No.: BP-501653 4.5

Ac4GlcNAlk is a peracetylated glucosamine-derived reagent bearing a terminal alkyne handle that can be used in click-based conjugation workflows. Structurally, it comprises a peracetylated sugar scaffold bearing an N-pent-4-ynoyl substituent with a terminal alkyne, providing a short, flexible linkage domain that can be appended to ligands or warheads through standard coupling chemistries while maintaining the stereochemical integrity typical of carbohydrate-based linkers. In PROTAC designs, such sugar–alkyl linkers can help tune the spatial relationship between the recruiting ligand and the E3 ligase-binding moiety, thereby influencing ternary complex formation and degradation efficiency. The acetylated character can also improve compatibility with common organic synthesis steps, facilitating stepwise assembly of multi-component constructs. Overall, Ac4GlcNAlk is valuable for researchers seeking reproducible linker architectures that modulate conjugate geometry and enable systematic structure–activity studies in targeted degradation research.

Structure of 1361993-37-4

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Category

PROTAC Linker

Molecular Formula

C₁₉H₂₅NO₁₀

Molecular Weight

427.40

* For research and manufacturing use only. Not for human or clinical use.

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Please store the product under the recommended conditions in the Certificate of Analysis.

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Room temperature in continental US; may vary elsewhere.

IUPACName

[(2R,3S,4R,5R)-3,4,6-triacetyloxy-5-(pent-4-ynoylamino)oxan-2-yl]methyl acetate

Synonyms

N-(4-pentynoyl)-glucosamine-tetraacylated (Ac4GlcAl)

InChI Key

PODQGPKRSTUNAT-ULAPBGCESA-N

InChI

InChI=1S/C19H25NO10/c1-6-7-8-15(25)20-16-18(28-12(4)23)17(27-11(3)22)14(9-26-10(2)21)30-19(16)29-13(5)24/h1,14,16-19H,7-9H2,2-5H3,(H,20,25)/t14-,16-,17-,18-,19?/m1/s1

SMILES

CC(=O)OCC1C(C(C(C(O1)OC(=O)C)NC(=O)CCC#C)OC(=O)C)OC(=O)C

1. Optimization of Metabolic Oligosaccharide Engineering with Ac4GalNAlk and Ac4GlcNAlk by an Engineered Pyrophosphorylase

Anna Cioce, Ganka Bineva-Todd, Anthony J Agbay, Junwon Choi, Thomas M Wood, Marjoke F Debets, William M Browne, Holly L Douglas, Chloe Roustan, Omur Y Tastan, Svend Kjaer, Jacob T Bush, Carolyn R Bertozzi, Benjamin Schumann ACS Chem Biol. 2021 Oct 15;16(10):1961-1967. doi: 10.1021/acschembio.1c00034.Epub 2021 Apr 9.

Metabolic oligosaccharide engineering (MOE) has fundamentally contributed to our understanding of protein glycosylation. Efficient MOE reagents are activated into nucleotide-sugars by cellular biosynthetic machineries, introduced into glycoproteins and traceable by bioorthogonal chemistry. Despite their widespread use, the metabolic fate of many MOE reagents is only beginning to be mapped. While metabolic interconnectivity can affect probe specificity, poor uptake by biosynthetic salvage pathways may impact probe sensitivity and trigger side reactions. Here, we use metabolic engineering to turn the weak alkyne-tagged MOE reagents Ac4GalNAlk and Ac4GlcNAlk into efficient chemical tools to probe protein glycosylation. We find that bypassing a metabolic bottleneck with an engineered version of the pyrophosphorylase AGX1 boosts nucleotide-sugar biosynthesis and increases bioorthogonal cell surface labeling by up to two orders of magnitude. A comparison with known azide-tagged MOE reagents reveals major differences in glycoprotein labeling, substantially expanding the toolbox of chemical glycobiology.

This PROTAC linker, Ac4GlcNAlk, is designed to support efficient conjugation between targeting ligands and E3-recruiting modules in targeted protein degradation workflows. Its features enable modular assembly under standard bioconjugation-compatible conditions, facilitating systematic exploration of linker length, flexibility, and attachment chemistry to optimize ternary complex formation and degradation potency. The details below describe its structural characteristics and practical reactivity considerations for PROTAC construction.

Structure: Ac4GlcNAlk comprises an acylated glucosamine-derived scaffold bearing an alkyl-reactive handle. It contains multiple oxygen and nitrogen heteroatoms that promote hydrogen bonding and polarity, with ester and amide functionalities that influence solubility, stability, and conjugation behavior in linker synthesis.

Reactivity: The linker is suitable for coupling strategies that use nucleophilic substitution or acyl-transfer logic, depending on the functional group presented during PROTAC assembly. Practical use typically involves activating the appropriate attachment site on the linker or partner ligand, then performing controlled conjugation in compatible organic or mixed solvent systems. Base-mediated conditions and mild catalysts are commonly selected to preserve labile ester/amide motifs while enabling selective bond formation.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂