(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

• ChemBase ID: 39083
• Molecular Formular: C24H20INO4
• Molecular Mass: 513.32437
• Monoisotopic Mass: 513.04370613
• SMILES: c1(ccc(cc1)C[C@@H](C(=O)O)NC(=O)OCC1c2c(c3c1cccc3)cccc2)I
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1ccc(cc1)I)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C24H20INO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1
• InChIKey: LXOXXTQKKRJNNB-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid
• Synonyms: 4-Iodo-L-phenylalanine, N-FMOC protected; N-(9-Fluorenylmethoxycarbonyl)-3-(4-iodophenyl)-L-alanine; Fmoc-4-iodo-L-phenylalanine; Fmoc-(4-iodo)-Phe-OH; Fmoc-4-iodo-L-phenylalanine; Fmoc-Phe(4-I)-OH; Fmoc-Phe(4-I)-OH; N-Fmoc-4-iodo-L-phenylalanine; N-芴甲氧羰基-L-4-碘苯丙氨酸; Fmoc-4-碘-L-苯丙氨酸; Fmoc-L-4-碘苯丙氨酸; N-Fmoc-4-碘-L-苯基丙氨酸

Database IDs

• CAS Number: 82565-68-2
• MDL Number: MFCD00672340
• Beilstein Number: 4592723
• PubChem SID: 24870532; 24870986; 161002390
• PubChem CID: 2761479

CALCULATED PROPERTIES

• Acid pKa: 3.167656
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.3229718
• LogD (pH = 7.4): 2.1796272
• Log P: 5.630588
• Molar Refractivity: 122.5586 cm^3
• Polarizability: 48.57136 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 213-217 °C(lit.); 213-217°C
• Optical Rotation: [α]22/D -10°, c = 1 in DMF; -10 (c=1 in DMF)

Safety Information

• Storage Warning: IRRITANT; Irritant; Light Sensitive
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0%; 95%; 97%
• Empirical Formula (Hill Notation): C24H20INO4

DETAILS

Sigma Aldrich - 47431

Other Notes
Synthesis of a phosphotyrosine mimetic1; Building block employed for the synthesis of peptides carrying a radio-label2
Packaging
1 g in poly tube
5 g in poly bottle