Benzyl {1,31-bis[(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranosyl)oxy]-16-[(3-{[3-({5-[(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranosyl)oxy]pentanoyl}amino)propyl]amino}- 3-oxopropoxy)methyl]-5,11,21,27-tetraoxo-14,18-dioxa-6,10,22,26-tetraazahentriacontan-16-yl}carbamate
[CAS# 1159408-63-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Benzyl {1,31-bis[(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranosyl)oxy]-16-[(3-{[3-({5-[(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranosyl)oxy]pentanoyl}amino)propyl]amino}- 3-oxopropoxy)methyl]-5,11,21,27-tetraoxo-14,18-dioxa-6,10,22,26-tetraazahentriacontan-16-yl}carbamate
• Synonyms: [(2R,3R,4R,5R,6R)-5-acetamido-6-[5-[3-[3-[3-[3-[3-[5-[(2R,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]-3-oxopropoxy]-2-[[3-[3-[5-[(2R,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentanoylamino]propylamino]-3-oxopropoxy]methyl]-2-(phenylmethoxycarbonylamino)propoxy]propanoylamino]propylamino]-5-oxopentoxy]-3,4-diacetyloxyoxan-2-yl]methyl acetate
• Molecular Formula: C₈₇H₁₃₄N₁₀O₃₈
• Molecular Weight: 1928.04
• CAS Registry Number: 1159408-63-5
• SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1OCCCCC(=O)NCCCNC(=O)CCOCC(COCCC(=O)NCCCNC(=O)CCCCO[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C)(COCCC(=O)NCCCNC(=O)CCCCO[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C)NC(=O)OCC4=CC=CC=C4)COC(=O)C)OC(=O)C)OC(=O)C

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.552, Calc.^*
• Boiling Point: 1646.7±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 949.7±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

Benzyl {1,31-bis[(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)oxy]-16-[(3-{[3-({5-[(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)oxy]pentanoyl}amino)propyl]amino}- 3-oxopropoxy)methyl]-5,11,21,27-tetraoxo-14,18-dioxa-6,10,22,26-tetraazahentriacontan-16-yl}carbamate is a highly specialized and complex glycopeptide conjugate, structured with multiple galactopyranosyl units and acetyl-protected groups, among other functionalities. This molecule exemplifies advancements in synthetic glycobiology, where carbohydrates are chemically combined with peptides or other biomolecules for targeted biological functions, such as specific binding or cell targeting. The intricate design of this molecule, involving acetamido and acetyl-protected galactopyranosyl moieties, positions it as an invaluable tool in biochemical research and therapeutic development, particularly in exploring protein-carbohydrate interactions.

The discovery and synthesis of this glycopeptide compound are part of a broader interest in understanding and mimicking the naturally occurring glycosylation found in cells, especially since glycosylation patterns play a crucial role in many biological processes, including cell signaling, immunity, and pathogen recognition. The ability to synthetically create such conjugates enables scientists to better study glycan interactions in a controlled manner. Using advanced organic synthesis techniques, researchers have developed this class of molecules to include specific galactose-containing glycan units that resemble those found on cell surfaces. By tailoring the structure to include protected acetamido groups and precise positioning of galactopyranosyl units, this molecule achieves stability, bioavailability, and specificity in binding interactions.

Applications of this glycopeptide conjugate are mainly focused on biological research and therapeutic potential. For instance, it is utilized in the study of glycan-lectin interactions, which are vital in processes like cell adhesion and immune response. Its structure allows it to mimic natural glycoproteins, making it valuable in assays that explore how glycan patterns affect cellular interactions with lectins or other receptors. This conjugate also holds promise in the development of targeted drug delivery systems, where its glycan motifs can direct it to specific cellular sites, enhancing the specificity and effectiveness of drugs, especially in cancer or inflammatory diseases. Additionally, these glycan structures are useful in creating synthetic vaccines, where the glycopeptide can simulate pathogen surface structures, potentially training the immune system to recognize and respond to real infections.

In the context of diagnostics, this glycopeptide compound’s defined carbohydrate units make it an ideal candidate for developing biosensors that can detect specific protein-carbohydrate interactions. Since certain disease markers are carbohydrate-binding proteins, biosensors using this molecule can achieve precise detection, enabling earlier diagnosis and better monitoring of diseases. The molecular complexity and specificity of this compound are thus contributing significantly to fields that rely on understanding and leveraging molecular recognition, such as immunology, oncology, and infectious disease research.

References

2021. LYTACs that engage the asialoglycoprotein receptor for targeted protein degradation. Nature Chemical Biology.
DOI: 10.1038/s41589-021-00770-1