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

• ChemBase ID: 38387
• Molecular Formular: C18H17NO4
• Molecular Mass: 311.33188
• Monoisotopic Mass: 311.11575803
• SMILES: C[C@@H](C(=O)O)NC(=O)OCC1c2c(c3c1cccc3)cccc2
• Canonical SMILES: O=C(N[C@H](C(=O)O)C)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/t11-/m0/s1
• InChIKey: QWXZOFZKSQXPDC-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid
• Synonyms: N-Alpha-Fmoc-L-alanine; Fmoc-L-alanine; Fmoc-Ala-OH; Fmoc-Ala-OH; N-(9-Fluorenylmethoxycarbonyl)-L-alanine; N-α-FMOC-L-ALANINE; N-(9-Fluorenylmethoxycarbonyl)-L-alanine monohydrate; Fmoc-Ala-OH.H2O; N-Fmoc-L-alanine monohydrate; N-芴甲氧羰基-L-丙氨酸; Fmoc-L-丙氨酸; N-Fmoc-L-丙氨酸单水合物

Database IDs

• CAS Number: 35661-39-3; 207291-76-7
• EC Number: 252-660-6
• MDL Number: MFCD00037139
• Beilstein Number: 2225975
• PubChem SID: 24877820; 24871215; 161001694
• PubChem CID: 6364642

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2873689
• LogD (pH = 7.4): -0.24262114
• Log P: 3.0453172
• Molar Refractivity: 84.5771 cm^3
• Polarizability: 33.993576 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 3.7422893

PROPERTIES

Physical Property

• Melting Point: 147-153 °C(lit.); ca 130°C
• Optical Rotation: [α]20/D -18°, c = 1 in DMF; [α]20/D -19±1°, c = 1% in DMF; -19 (c=1 in DMF)

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: IRRITANT
• 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: ≥95.0% (T); 95%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C18H17NO4

DETAILS

Sigma Aldrich - 531480

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 47616

Other Notes
FMOC-protected amino acids are widely used in solid phase peptide synthesis1