118358-38-6

Basic information

• Product Name: FMOC-L-SER(BETA-D-GLCAC4)-OH
• Synonyms: FMOC-L-SER(BETA-D-GLCAC4)-OH;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-L-SERINE;Fmoc-L-Ser(β-D-Glc(Ac)4)-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-L-serine
• CAS NO: 118358-38-6
• Molecular Formula: C₃₂H₃₅NO₁₄
• Molecular Weight: 657.62
• Product Categories: Glycoamino Acid
• Mol File: 118358-38-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 775.0±60.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• PKA: 3.34±0.10(Predicted)
• CAS DataBase Reference: FMOC-L-SER(BETA-D-GLCAC4)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-SER(BETA-D-GLCAC4)-OH(118358-38-6)
• EPA Substance Registry System: FMOC-L-SER(BETA-D-GLCAC4)-OH(118358-38-6)

Safety Data

• Hazardous Substances Data: 118358-38-6(Hazardous Substances Data)

Usage

General Description

The chemical FMOC-L-Ser(Beta-D-GlcAC4)-OH is a derivative of L-Serine, an amino acid that is commonly found in proteins and enzymes. The FMOC group serves as a protective group that can be removed under specific conditions. The addition of Beta-D-GlcAC4 refers to the presence of a beta-D-glucosamine molecule with an acetyl group at the 4th position. This modification may be used to study or manipulate biological processes related to the carbohydrate moiety, such as glycosylation. Overall, FMOC-L-Ser(Beta-D-GlcAC4)-OH is a specialized chemical compound that can be used in research and synthetic chemistry applications.

Upstream product

• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 136497-85-3 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionic acid allyl ester 

Downstream Products

• 175854-13-4 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(S)-2-(4-nitro-phenylcarbamoyl)-pyrrolidin-1-yl]-3-oxo-propoxy}-tetrahydro-pyran-3-yl ester 
• 145362-69-2 C₄₃H₆₂N₁₀O₁₆S₂ 
• 1181341-93-4 H-Tyr-D-Ala-Gly-Phe-Nle-Pro-Leu-Ser(Glc)-Trp-NH-3,5-Bzl(CF₃)2 
• 1181341-90-1 H-Tyr-D-Ala-Gly-Phe-Ser(Glc)-Pro-Leu-Trp-NH-3,5-Bzl(CF₃)2 
• 1181341-91-2 H-Tyr-D-Ala-Gly-Phe-Nle-Ser(Glc)-Leu-Trp-NH-3,5-Bzl(CF₃)2 
• 1181341-92-3 H-Tyr-D-Ala-Gly-Phe-Nle-Pro-Ser(Glc)-Trp-NH-3,5-Bzl(CF₃)2 

Relevant articles and documents

Evaluation of a carbohydrate-π interaction in a peptide model system

A carbohydrate-π interaction contributes -0.8 kcal mol-1 to the stabilization of a β-hairpin peptide. The Royal Society of Chemistry.

Folding-induced CO2-soluble peptides

The first CO2- and water-soluble peptide is reported, in which folding facilitates its solubility in CO2. The Royal Society of Chemistry.

Effects of Glycosylation and d -Amino Acid Substitution on the Antitumor and Antibacterial Activities of Bee Venom Peptide HYL

Glycosylation is a promising strategy for modulating the physicochemical properties of peptides. However, the influence of glycosylation on the biological activities of peptides remains unknown. Here, we chose the bee venom peptide HYL as a model peptide and 12 different monosaccharides as model sugars to study the effects of glycosylation site, number, and monosaccharide structure on the biochemical properties, activities, and cellular selectivities of HYL derivatives. Some analogues of HYL showed improvement not only in cell selectivity and proteolytic stability but also in antitumor and antimicrobial activity. Moreover, we found that the helicity of glycopeptides can affect its antitumor activity and proteolytic stability, and the α-linked d-monosaccharides can effectively improve the antitumor activity of HYL. Therefore, it is possible to design peptides with improved properties by varying the number, structure, and position of monosaccharides. What's more, the glycopeptides HYL-31 and HYL-33 show a promising prospect for antitumor and antimicrobial drugs development, respectively. In addition, we found that the d-lysine substitution strategy can significantly improve the proteolytic stability of HYL. Our new approach provides a reference or guidance for the research of novel antitumor and antimicrobial peptide drugs.

Facile synthesis of glycosylated Fmoc amino acid building blocks assisted by microwave irradiation

The synthesis of glycosylated Fmoc amino acids by reaction of mono- and disaccharide peracetates with Fmoc amino acids having free carboxyl groups was rapidly promoted by Lewis acids (SnCl4, BF3·Et 2O) under microwave irradiation. The products are useful building blocks for the synthesis of glycopeptides.