111524-95-9

Basic information

• Product Name: FMOC-D-PHG-OH
• Synonyms: (R)-[(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)]-PHENYL-ACETIC ACID;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-PHENYLGLYCINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-PHENYLGLYCINE;N-ALPHA-FMOC-D-PHENYLGLYCINE;RARECHEM EM WB 0180;FMOC-D-PHENYLGLYCINE;FMOC-D-(PHENYL)GLY-OH;FMOC-D-PHG-OH
• CAS NO: 111524-95-9
• Molecular Formula: C₂₃H₁₉NO₄
• Molecular Weight: 373.4
• EINECS: 1533716-785-6
• Product Categories: Fluorenes, Flurenones;Amino Acids;Phenylglycine [Phg];Unusual Amino Acids;Fmoc-Amino acid series
• Mol File: 111524-95-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 170-180°C
• Boiling Point: 606.3 °C at 760 mmHg
• Flash Point: 320.5 °C
• Appearance: /Solid
• Density: 1.299 g/cm³
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 3.39±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-PHG-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-PHG-OH(111524-95-9)
• EPA Substance Registry System: FMOC-D-PHG-OH(111524-95-9)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 111524-95-9(Hazardous Substances Data)

Usage

Description

FMOC-D-PHG-OH, also known as N-(9-fluorenylmethoxycarbonyl)-D-phenylglycine, is an amino acid derivative commonly utilized in the field of peptide chemistry. It is a white powder with specific chemical properties that make it a valuable component in the synthesis of peptides and related bioactive molecules.

Uses

Used in Pharmaceutical Industry:
FMOC-D-PHG-OH is used as a building block for the synthesis of various peptides and peptide-based drugs. Its application is primarily due to its ability to facilitate the formation of peptide bonds, which are crucial for the structure and function of proteins and peptides.
Used in Research and Development:
In the research and development sector, FMOC-D-PHG-OH is used as a key component in the design and synthesis of novel bioactive peptides. Its role in this context is to provide a stable and versatile platform for the exploration of new peptide sequences and their potential applications in medicine and biotechnology.
Used in Chemical Synthesis:
FMOC-D-PHG-OH is also employed in chemical synthesis processes, where it serves as a protected amino acid derivative. This protection is essential for preventing unwanted side reactions during the synthesis of complex peptide structures, ensuring the desired product is obtained with high purity and yield.
Overall, FMOC-D-PHG-OH is a versatile and essential compound in the fields of pharmaceuticals, research and development, and chemical synthesis, playing a crucial role in the creation of new peptide-based therapies and bioactive molecules.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 69-91-0 L-α-phenylglycine 
• 875-74-1 (R)-phenylglycine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 163883-97-4 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-phenylacetic acid 
• 2835-06-5 phenylglycin 
• 470670-74-7 2,5-dioxo-4-phenyl-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 

Downstream Products

• 120061-01-0 Fmoc-Phg-MePhe-Thz-OTmse 
• 120061-01-0 Fmoc-D-Phg-MePhe-Thz-OTmse 
• 111524-97-1 Fmoc-D-Phg-Cl 
• 852866-05-8 Fmoc-D-Phg-Phe-OH 
• 120061-03-2 Phg-MePhe-Thz 
• 120061-02-1 Phg-MePhe-Thz-OTmse 
• 1359870-36-2 Fmoc-D-Phg-SH 
• 111524-87-9 methyl 2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetamido)-3-phenylpropanoate 
• 1417604-08-0 C₃₆H₂₇BrN₂O₄ 
• 1417603-94-1 C₃₈H₃₀N₂O₄ 
• 1417604-13-7 C₄₅H₃₉N₃O₅ 
• 1417604-14-8 C₄₅H₃₉N₃O₅ 
• 1417603-98-5 C₃₀H₂₉N₃O₃ 
• 1417603-99-6 C₃₀H₂₉N₃O₃ 

Relevant articles and documents

Discovery of a Highly Potent, Cell-Permeable Macrocyclic Peptidomimetic (MM-589) Targeting the WD Repeat Domain 5 Protein (WDR5)-Mixed Lineage Leukemia (MLL) Protein-Protein Interaction

We report herein the design, synthesis, and evaluation of macrocyclic peptidomimetics that bind to WD repeat domain 5 (WDR5) and block the WDR5-mixed lineage leukemia (MLL) protein-protein interaction. Compound 18 (MM-589) binds to WDR5 with an IC50 value of 0.90 nM (Ki value 50 value of 12.7 nM. Compound 18 potently and selectively inhibits cell growth in human leukemia cell lines harboring MLL translocations and is >40 times better than the previously reported compound MM-401. Cocrystal structures of 16 and 18 complexed with WDR5 provide structural basis for their high affinity binding to WDR5. Additionally, we have developed and optimized a new AlphaLISA-based MLL HMT functional assay to facilitate the functional evaluation of these designed compounds. Compound 18 represents the most potent inhibitor of the WDR5-MLL interaction reported to date, and further optimization of 18 may yield a new therapy for acute leukemia.

Development of a rapid, room-temperature dynamic kinetic resolution for efficient asymmetric synthesis of α-aryl amino acids

equation presented A rapid, highly efficient and general dynamic kinetic resolution (DKR) of racemic α-aryl UNCAs with the dual-function catalysis of modified cinchona alkaloid was accomplished at room temperature. This DKR led to the development of a highly enantioselective catalytic method for the practical synthesis of a wide range of α-aryl and α-heteroaryl amino acids in 89-92% ee and 86-95% yield from racemic UNCAs.

SIMULTANEOUS USE OF N-Fmoc AND OTmse PROTECTIVE GROUPS IN THE SYNTHESIS OF PEPTOLYTIC SENSITIVE PEPTIDES

The combined use of Fmoc (fluorenylmethoxycarbonyl) as N-protection and Tmse (trimethylsilylethyl) as O-protection during demanding fragment condensation mediated by Bop-Cl (N,N'-bis(3-oxo-2-oxazolidinyl)phosphinyl chloride) has been explored in the preparation of useful synthons that are sensitive to acidic and even basic hydrolyses.Stepwise deprotection by morfoline (Fmoc-deprotection) followed by F--mediated removal of Tmse results in a very effective peptide synthesis strategy, as exemplified by the preparation of i.a.Phg-MePhe-Thz.Similarly, combinations of N-Boc, O-Tmse peptide esters are also possible that allow the preparation of +H2-MePhe-Thz-OTmse (via Boc-MePhe-Thz-OTmse) without competitive DKP formation.