5-[4-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3,5-dimethoxyphenoxy]pentanoic acid

• ChemBase ID: 156154
• Molecular Formular: C29H31NO7
• Molecular Mass: 505.55894
• Monoisotopic Mass: 505.21005234
• SMILES: COc1cc(cc(c1CNC(=O)OCC1c2ccccc2c2c1cccc2)OC)OCCCCC(=O)O
• Canonical SMILES: COc1cc(OCCCCC(=O)O)cc(c1CNC(=O)OCC1c2ccccc2c2c1cccc2)OC
• InChI: InChI=1S/C29H31NO7/c1-34-26-15-19(36-14-8-7-13-28(31)32)16-27(35-2)24(26)17-30-29(33)37-18-25-22-11-5-3-9-20(22)21-10-4-6-12-23(21)25/h3-6,9-12,15-16,25H,7-8,13-14,17-18H2,1-2H3,(H,30,33)(H,31,32)
• InChIKey: ATYUCXIJDKHOPX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[4-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3,5-dimethoxyphenoxy]pentanoic acid
• IUPAC Traditional name: 5-[4-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3,5-dimethoxyphenoxy]pentanoic acid
• Synonyms: 5-[3,5-Dimethoxy-4-(Fmoc-aminomethyl)phenoxy]pentanoic acid; N-Fmoc-PAL Linker; 5-[4-[[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]methyl]-3,5-dimethoxyphenoxy]-pentanoic Acid; Fmoc-PAL; 5-[3,5-二甲氧基-4-(Fmoc-氨甲基)苯氧基]戊酸; N-Fmoc-PAL 连接基

Database IDs

• CAS Number: 115109-65-4
• MDL Number: MFCD00236731
• Beilstein Number: 4219682
• PubChem SID: 162250292; 24844949
• PubChem CID: 130773

CALCULATED PROPERTIES

• Acid pKa: 3.5037098
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.710147
• LogD (pH = 7.4): 1.3239805
• Log P: 4.6982546
• Molar Refractivity: 138.1408 cm^3
• Polarizability: 54.823673 Å^3
• Polar Surface Area: 103.32 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C29H31NO7

DETAILS

Sigma Aldrich - 00755

Other Notes
Handle for the mild solid-phase synthesis of C-terminal peptide amides1

Toronto Research Chemicals - F657500

Used in the solid-phase peptide synthesis (SPPS).

REFERENCES

• Kahn, S., et al.: Diabetes, 39, 634 (1990)
• Abedini, A., et al.: Biochemistry, 44, 16284 (1990)