Is Fmoc stable in DIPEA?
Fmoc is stable under the cleavage conditions of Aloc/All (Pd°). Towards tertiary amines such as DIPEA, pyridine [1]; the relative stability depends on base concentration, solvent and temperature. Stability towards hydrogenolysis is controversial [2] and should be evaluated for each individual case.
Is Fmoc stable in TFA?
It is stable in 50% TFA, but is removed under the standard peptide cleavage conditions (e.g. HF, TFMSOTf, TFSMA, HBr/AcOH). The Fmoc group is acid stable and Boc-Lys(Fmoc)-OH is used to prepare protected peptide fragments for fragment coupling.
Does TFA Deprotect Fmoc?
In the Fmoc synthesis, trifluoroacetic acid (TFA) is usually employed as a deprotecting agent at high concentration (90–95%).
What group does Fmoc protect?
The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile protecting group used in organic synthesis.
What is FMOC used for?
Definition. FMOC chemistry describes a peptide synthesis strategy in which the 9-fluorenylmethoxycarbonyl group (Fmoc group) is used as a temporary protecting group for the N‐terminus. The Fmoc group is cleaved by secondary amines like piperidine.
What group does FMOC protect?
Why is Fmoc used in peptide synthesis?
The use of N-terminal Fmoc protection allows for a milder deprotection scheme than used for Boc/Bzl SPPS, and this protection scheme is truly orthogonal under SPPS conditions.
What is the role of Fmoc?
Fmoc is widely used as a main amine protecting group in peptide synthesis. 17-19 The intrinsic hydrophobicity and aromaticity of Fmoc is well-known to promote the hydrophobic and π-π stacking interactions of the fluorenyl rings.
How do I get rid of Fmoc group?
The Fmoc group is, in general, rapidly removed by primary (i.e., cyclohexylamine, ethanolamine) and some secondary (i.e., piperidine, piperazine) amines, and slowly removed by tertiary (i.e., triethylamine [Et3N], N, N-diisopropylethylamine [DIEA]) amines.
How do you quench a TFA?
To remove traces of TFA you can use exsiccator with KOH and – optionally – some heat. If you have the salt with TFA you could dissolve your product in water add some NH3 – until you have slight alkalline conditions – and extract your product with CHCl3 or DCM, evaporate and dry over KOH.
What does Fmoc stand for chemistry?
What is the cleavage stability of Fmoc?
Fmoc is acid-stable, withstands cleavage of Boc/tBu (TFA) and Z/Bzl (HF). Fmoc is stable under the cleavage conditions of Aloc/All (Pd°).
What is the stability of the ionic compound Fmoc?
Fmoc is stable under the cleavage conditions of Aloc/All (Pd°). Towards tertiary amines such as DIPEA, pyridine [1]; the relative stability depends on base concentration, solvent and temperature. Stability towards hydrogenolysis is controversial [2] and should be evaluated for each individual case.
What is the Fmoc deprotection step?
Furthermore, the Fmoc deprotection step is one of the most crucial stages in peptide synthesis (besides amino acids coupling). Most importantly, the property which makes the Fmoc group a valuable tool in SPPS is its selective base-mediated removal while leaving the other, acid-labile side-chain protecting groups intact.
What is the CAS and EC number for Fmoc-Cl?
Fmoc chloride 97%; CAS Number: 28920-43-6; EC Number: 249-313-6; Synonyms: 9-Fluorenylmethoxycarbonyl chloride,9-Fluorenylmethyl chloroformate,Fmoc-Cl; find Sigma-Aldrich-160512 MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich