118358-80-8

Basic information

• Product Name: Tetra-O-acetyl-a-Mannosyl-Fmocserine
• Synonyms: Tetra-O-acetyl-a-Mannosyl-Fmocserine;2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl-Fmoc serine;Fmoc-L-Ser(α-D-Man(Ac)4)-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-L-serine;Man-Ser
• CAS NO: 118358-80-8
• Molecular Formula: C₃₂H₃₅NO₁₄
• Molecular Weight: 657.62
• Product Categories: Glycoamino Acid
• Mol File: 118358-80-8.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Tetra-O-acetyl-a-Mannosyl-Fmocserine(CAS DataBase Reference)
• NIST Chemistry Reference: Tetra-O-acetyl-a-Mannosyl-Fmocserine(118358-80-8)
• EPA Substance Registry System: Tetra-O-acetyl-a-Mannosyl-Fmocserine(118358-80-8)

Safety Data

• Hazardous Substances Data: 118358-80-8(Hazardous Substances Data)

Usage

Uses

2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl-Fmoc serine (CAS# 118358-80-8) is a an fmoc-protected, and glycosylated form of L-serine (S270995) used in the synthetic preparation of peptides and peptide fragments, such as the synthesis of homogeneously glycosylated insulin for use as an oral medication for diabetics.

Upstream product

• 136497-85-3 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionic acid allyl ester 
• 118358-79-5 N-Fmoc-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine benzyl ester 
• 83-87-4 D-Mannose pentaacetate 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 168566-64-1 N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine allyl ester 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 
• 13242-53-0 acetobromomannose 
• 118358-66-0 N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 935457-93-5 (S)-2-Amino-3-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid 

Downstream Products

• 216309-87-4 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 211678-18-1 -D-glutamic acid 1-methylamide 5-benzyl ester 
• 211678-13-6 -D-glutamic acid 1-methylamide 5-benzyl ester 
• 211678-12-5 -L-glutamic acid 1-methylamide 5-benzyl ester 

Relevant articles and documents

Antibacterial cyclic D,L-α-glycopeptides

We report the design, synthesis, membrane activity, biophysical characterization, and in vitro antibacterial activities of cationic cyclic d,l-α-glycopeptides bearing d-glucosamine (GlcNH2), d-galactose (Gal), or d-mannose (Man) glycosyl side chains.

Synthesis of high functionality and quality mannose-grafted lipids to produce macrophage-targeted liposomes

The mannose receptor, which is responsible for tumor invasion, proliferation, and metastasis in the tumor microenvironment, is overexpressed in tumor-associated macrophages. Mannose is commonly applied to PEGylated liposomes in macrophage-targeted cancer therapy. To develop a high functionality and quality (HFQ) lipid for macrophage-targeted liposomes, we designed a novel mannosylated lipid with improved mannose receptor binding affinity using serine–glycine repeats (SG)n. We synthesized Man(S)-(SG)5-SSK-K(Pal)2 using only a fluorenylmethyloxycarbonyl (Fmoc) protecting group solid-phase peptide synthesis method, which produced a high-quality lipid at a moderately good yield. We then prepared Man-(SG)5/PEGylated liposomes using a post-insertion technique to insert Man(S)-(SG)5-SSK-K(Pal)2 into the PEGylated liposomes. In vitro cell investigations revealed that the Man-(SG)5/PEGylated liposomes effectively associated with mouse peritoneal macrophages by interacting with the mannose receptors. The results suggest that we produced a novel high-quality, highly functional mannosylated lipid that is suitable for clinical drug delivery applications.

A convenient and efficient synthetic approach to mono-, di-, and tri-O-mannosylated Fmoc amino acids

A convenient and highly efficient synthesis of mono-, di-, and tri-O-mannosylated Fmoc-Ser and Thr is described. The short synthetic route and high overall yield highlight the synthetic utility of this unified approach.