8.52017

Fmoc-Pro-OH

Novabiochem^®

• Synonym(s): Fmoc-Pro-OH, N-α-Fmoc-L-proline
• Empirical Formula (Hill Notation): C₂₀H₁₉NO₄
• CAS Number: 71989-31-6
• Molecular Weight: 337.37
• UNSPSC Code: 12352209
• EC Index Number: 276-259-0
• NACRES: NA.22
• MDL number: MFCD00037122

Properties

• Quality Segment: 400
• product line: Novabiochem^®
• assay: ≥94.0% (acidimetric), ≥98% (TLC), ≥99.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• mp: 112-115 °C
• application(s): peptide synthesis
• functional group: Fmoc
• storage temp.: 2-30°C
• SMILES string: N4(C(CCC4)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C20H19NO4/c22-19(23)18-10-5-11-21(18)20(24)25-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,22,23)
• InChI key: ZPGDWQNBZYOZTI-UHFFFAOYSA-N

Description

General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities.
Standard building block for introduction of proline amino-acid residues by Fmoc SPPS

Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS

Application

• Biphasic electrochemical peptide synthesis: This study highlights the application of Fmoc-Pro-OH in electrochemical peptide synthesis, where slight excesses of reagents and electricity were required, possibly due to steric hindrance (S Nagahara, Y Okada, Y Kitano, K Chiba - Chemical Science, 2021).


• Elucidation of the Mechanism of Endo-XaaC-terminal Peptide Impurity Formation in SPPS: Fmoc-Pro-OH′s role was analyzed in a study investigating impurity formation during solid-phase peptide synthesis, highlighting its distinctively low tendency to form impurities (Y Yang, L Hansen, A Baldi - Organic Process Research & Development, 2021).


• Polymer–peptide delivery platforms: This research utilized Fmoc-Pro-OH in the development of polymer-based DNA delivery systems, emphasizing the effect of oligopeptide orientation on delivery efficacy (SS Parelkar, R Letteri, D Chan-Seng - Biomacromolecules, 2014).


• Structure–Activity Relationship Study of N-Hydroxyphtalimide Derivatives: The study explored the use of Fmoc-Pro-OH in the synthesis of N-Hydroxyphtalimide derivatives for detecting amines during peptide synthesis (K Takamatsu, R Suzuki, A Matsunaga - The Journal of Organic Chemistry, 2023).

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.8 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-β-Ala-Pro-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Pro-Pro-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (GC): ≤ 0.2 %
Purity (TLC(011A)): ≥ 98 %
Solubility (25 mmole in 50 ml DMF): clearly soluble
Assay (acidimetric): ≥ 94.0 %
Water (K. F.): ≤ 6.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.02 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1031

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable