189937-46-0

Basic information

• Product Name: FMOC-D-3,3-DIPHENYLALANINE
• Synonyms: RARECHEM BK PT 0198;N-FMOC-BETA-PHENYL-D-PHENYLALANINE;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-BETA-PHENYL-D-PHENYLALANINE;N-(9-FLUORENYLMETHOXYCARBONYL)-BETA-PHENYL-D-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-3,3-DIPHENYLALANINE;FMOC-D-DPH-OH;FMOC-D-(3-PHENYL)PHE-OH;FMOC-D-3,3-DIPHENYLALANINE
• CAS NO: 189937-46-0
• Molecular Formula: C30H25NO4
• Molecular Weight: 463.52
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;Peptide;a-amino;unnatural amino acids
• Mol File: 189937-46-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 116.5-119.5 °C(lit.)
• Boiling Point: 676.5oC at 760 mmHg
• Flash Point: 362.9oC
• Appearance: /
• Density: 1.262g/cm3
• Vapor Pressure: 3.18E-19mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Store at 0°C
• PKA: 3.57±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-3,3-DIPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-3,3-DIPHENYLALANINE(189937-46-0)
• EPA Substance Registry System: FMOC-D-3,3-DIPHENYLALANINE(189937-46-0)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 189937-46-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Fmoc-d-3,3-diphenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

InChI:InChI=1/C30H25NO4/c32-29(33)28(27(20-11-3-1-4-12-20)21-13-5-2-6-14-21)31-30(34)35-19-26-24-17-9-7-15-22(24)23-16-8-10-18-25(23)26/h1-18,26-28H,19H2,(H,31,34)(H,32,33)/t28-/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 62653-26-3 2-amino-3,3-diphenylpropionic acid 

Downstream Products

• 1213773-79-5 O-W-F-I-Dip-H(1-Bzl)-NH₂ 
• 1213773-14-8 O-W-Dip-I-F-H(1-Bzl)-NH₂ 
• 1282610-49-4 C₂₇H₄₀N₁₀O₃ 
• 1610523-60-8 HO-Leu-N-Me-Val-D-Leu-D-Phe-3,3-diphenyl-D-Ala-NH₂ 
• 1610523-72-2 HO-Leu-N-Me-Val-D-Leu-D-3-(2-pyridyl)Ala-3,3-diphenyl-D-Ala-NH₂ 
• 1610523-73-3 HO-Leu-N-Me-Val-D-Leu-D-3-(3-pyridyl)Ala-3,3-diphenyl-D-Ala-NH₂ 
• 1610523-74-4 HO-Leu-N-Me-Val-D-Leu-D-3-(4-pyridyl)Ala-3,3-diphenyl-D-Ala-NH₂ 
• 1610523-76-6 HO-Leu-N-Me-Val-D-Leu-D-Tyr(Me)-3,3-diphenyl-D-Ala-NH₂ 

Relevant articles and documents

The effects of conformational constraints and steric bulk in the amino acid moiety of philanthotoxins on AMPAR antagonism

Philanthotoxin-343 (PhTX-343), a synthetic analogue of wasp toxin PhTX-433, is a noncompetitive antagonist at ionotropic receptors (e.g., AChR or iGluR). To determine possible effects of variations of the amino acid side chain, a library consisting of seventeen PhTX-343 analogues was prepared. Thus, tyrosine was replaced by either apolar, conformationally constrained, or bulky amino acids, whereas the acyl unit and the polyamine moiety were kept unchanged. Analogues with tertiary amide groups were prepared for the first time. Pentafluorophenyl esters were employed for amide bond formation, establishing general protocols for philanthotoxin solution- and solid-phase synthesis (39-90% and 42-54% overall yields, respectively). The analogues were tested for their ability to antagonize kainate-induced currents of 2-amino-3-(3-hydroxy-5-methyl- 4-isoxazoyl)propanoic acid receptors (AMPAR) expressed in Xenopus oocytes from rat brain mRNA. This showed that steric bulk in the amino acid moiety is well tolerated and suggests that binding to AMPAR does not involve the α-NHCO group as a donor in hydrogen bonding.