171778-17-9

Basic information

• Product Name: FMOC-SER(AC)-OH
• Synonyms: N-ALPHA-FMOC-O-ACETYL-L-SERINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-ACETYL-L-SERINE;FMOC-O-ACETYL-L-SERINE;FMOC-SERINE(AC)-OH;FMOC-SER(AC)-OH;O-Acetyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine;Fmoc-O-acetyl-L-serine99%;(9H-Fluoren-9-yl)MethOxy]Carbonyl Ser(Ac)-OH
• CAS NO: 171778-17-9
• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.37
• Mol File: 171778-17-9.mol

Chemical Properties

• Boiling Point: 611.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.322
• Storage Temp.: 2-8°C
• PKA: 3.27±0.10(Predicted)
• CAS DataBase Reference: FMOC-SER(AC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-SER(AC)-OH(171778-17-9)
• EPA Substance Registry System: FMOC-SER(AC)-OH(171778-17-9)

Safety Data

• Hazardous Substances Data: 171778-17-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
FMOC-SER(AC)-OH is used as a building block for the synthesis of peptides and proteins, which are essential components of various pharmaceutical products. The acetyl group attached to the serine amino acid allows for specific chemical reactions to occur, enabling the creation of unique peptide and protein structures with desired properties.
Used in Research and Development:
FMOC-SER(AC)-OH is used as a research tool in the development of new drugs and therapies. Its ability to modify the reactivity and properties of the serine amino acid makes it a valuable component in the design and synthesis of novel peptide-based therapeutic agents.
Used in Chemical Synthesis:
FMOC-SER(AC)-OH is used as a reagent in the chemical synthesis of various compounds. The temporary protective FMOC group allows for controlled reactions, ensuring the desired product is obtained without unwanted side reactions.
Used in Biochemistry and Molecular Biology:
FMOC-SER(AC)-OH is used in the study of protein structure and function. The ability to modify the serine amino acid with an acetyl group allows researchers to investigate the effects of specific modifications on protein folding, stability, and interactions with other biomolecules.

Upstream product

• 31077-89-1 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 5147-00-2 O-acetyl-L-serine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 286463-65-8 (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate 
• 886443-07-8 (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate 
• 959859-99-5 (Z)-1-(3,4,5-trimethoxphenyl)-2-(3'-amino-4'-difluoromethoxyphenyl)-ethene-3'-N-serinamide 
• 1017294-04-0 C₅₈H₅₆N₄O₁₄ 
• 1204138-98-6 C₃₉H₄₀N₂O₉ 

Relevant articles and documents

Synthesis method of Na-9-fluorenylmethoxycarbonyl-O-acetyl-L-serine

The invention relates to a synthesis method of Na-9-fluorenylmethoxycarbonyl-O-acetyl-L-serine, mainly aiming at solving the technical problems that in the existing synthesis method, the aftertreatment operation is more troublesome since perchloric acid is taken as a catalyst, excessive acetyl chloride is used, and potential safety hazard is caused when ethyl ether is used for crystallizing. The method comprises the following steps: (1) dissolving solid L-serine into an acetic acid solution, dropwise adding liquid acetyl chloride, and stirring for carrying out reaction; adding the reaction liquid into a petroleum ether solution, separating out an intermediate O-acetyl-L-serine, filtering and drying; (2) dissolving the intermediate into a sodium carbonate solution, dropwise adding a 9-fluorene methyl-N-succinimido-carbonate solution dissolved in ethyl acetate, removing the excessive 9-fluorene methyl-N-succinimido-carbonate in a layering way, acidifying the water phase by using hydrochloric acid, then extracting by using an extracting agent-ethyl acetate, washing the obtained oil phase with water, removing the hydrochloric acid, and concentrating the oil phase for removing the extracting agent-ethyl acetate so as to obtain the white crystal Na-9-fluorenylmethoxycarbonyl-O-acetyl-L-serine product. The product synthesized by the method is an important raw material for synthesizing polypeptide drugs.

Utility of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[18F] fluoroglucopyranoside for no-carrier-added18F-glycosylation of amino acids

A radiochemical method for the 18F-glycosylation of amino acid side chains was developed starting from peracetylated 2-deoxy-2-[ 18F]fluoroglucopyranoside (TA-[18F]FDG). O-(2-deoxy-2-[18F]fluoro-D-glucopyranosyl)-L-serine and the corresponding threonyl compound were obtained in a radiochemical yield of 25% and 12% (related to [18F]fluoride), respectively, after Zemplen deprotection within a total reaction time of 90 min. The anomeric configuration of the corresponding 19F-substituted compounds revealed preferential α-stereoselectivity. The 18F- glycosylation method using TA-[18F]FDG is compatible with the short half-life of fluorine-18 and combines glycosylation and 18F-labelling of a target compound within a single reaction step. TA-[18F]FDG is a promising 18F-labelled prosthetic group and could be adapted to 18F-labelling of bioactive peptides to study their pharmacokinetics using positron emission tomography (PET). Copyright