(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoic acid

• ChemBase ID: 103270
• Molecular Formular: C26H22N2O4
• Molecular Mass: 426.46388
• Monoisotopic Mass: 426.15795719
• SMILES: OC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OCC1c2c(cccc2)c2c1cccc2
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C26H22N2O4/c29-25(30)24(13-16-14-27-23-12-6-5-7-17(16)23)28-26(31)32-15-22-20-10-3-1-8-18(20)19-9-2-4-11-21(19)22/h1-12,14,22,24,27H,13,15H2,(H,28,31)(H,29,30)/t24-/m0/s1
• InChIKey: MGHMWKZOLAAOTD-DEOSSOPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoic acid; fmoc-tryptophan
• Synonyms: Fmoc-L-tryptophan; Fmoc-Trp-OH; Fmoc-Trp-OH; N-α-FMOC-L-TRYPTOPHAN; N(alpha)-9-Fluorenylmethoxycarbonyl-L-tryptophan; N(alpha)-Fmoc-L-tryptophan; Fmoc-L-色氨酸; N(α)-Fmoc-L-色氨酸

Database IDs

• CAS Number: 35737-15-6
• EC Number: 252-706-5
• MDL Number: MFCD00037126
• Beilstein Number: 4216624
• PubChem SID: 24865587; 24871246; 162103291
• PubChem CID: 978343

CALCULATED PROPERTIES

• Acid pKa: 3.9221783
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.2160797
• LogD (pH = 7.4): 1.5984135
• Log P: 4.8004055
• Molar Refractivity: 120.2826 cm^3
• Polarizability: 48.821014 Å^3
• Polar Surface Area: 91.42 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 182-185 °C(lit.); 182-185°C
• Optical Rotation: [α]20/D -28°, c = 1 in DMF; [α]20/D -29±1°, c = 1% in DMF; -27 (c=1 in DMF)

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); 97%; 98%
• Impurities: <3% ethyl acetate
• Empirical Formula (Hill Notation): C26H22N2O4

DETAILS

Sigma Aldrich - 47637

Packaging
5 g in glass bottle

Sigma Aldrich - 408689

Application
Cyclic peptides used as tachykinin antagonists have been prepared from Fmoc-protected D- and L- tryptophans.1,2