Understanding the Chemistry of H-Orn(Tfa)-OH: Structure and Synthesis Insights
The field of chemistry relies on a deep understanding of molecular structures and how they are synthesized. N-delta-Trifluoroacetyl-ornithine (H-Orn(Tfa)-OH), a derivative of the naturally occurring amino acid ornithine, is a prime example of a compound whose utility is directly linked to its well-defined structure and controlled synthesis.
At its core, H-Orn(Tfa)-OH is ornithine, a non-essential amino acid. Ornithine has a five-carbon chain with an alpha-amino group and a carboxyl group. What distinguishes H-Orn(Tfa)-OH is the modification at the delta-amino group (the amino group on the fifth carbon) with a trifluoroacetyl (TFA) group. The chemical formula is C7H11F3N2O3, and its molecular weight is approximately 228.17 g/mol. The trifluoroacetyl group (-COCF3) is a common protecting group in organic synthesis due to its stability and the ease with which it can be removed under specific acidic conditions.
The synthesis of H-Orn(Tfa)-OH typically involves the selective acylation of the delta-amino group of ornithine. This is often achieved using trifluoroacetic anhydride or a similar trifluoroacetylating agent in the presence of a base or under controlled solvent conditions. Protecting the delta-amino group is crucial because ornithine has two amino groups, and selective reactions are often required in peptide synthesis or the construction of more complex molecules. The alpha-amino group and the carboxyl group remain available for subsequent reactions after the delta-amino group is protected.
The resulting H-Orn(Tfa)-OH is a versatile building block. Its structure allows it to be incorporated into peptide chains, serve as an intermediate in the synthesis of heterocyclic compounds, or be used in various organic transformations where a protected ornithine moiety is beneficial. The presence of the fluorine atoms in the TFA group can also influence the physical properties and reactivity of the molecule, making it unique compared to other protected amino acids.
For researchers and chemical manufacturers, reliable synthesis routes and high-purity products are essential. NINGBO INNO PHARMCHEM CO.,LTD., as a China-based supplier, ensures that H-Orn(Tfa)-OH is synthesized with precision, meeting the demanding specifications required for advanced chemical applications. Understanding the synthesis and structure of such compounds is fundamental to pushing the boundaries of chemical innovation.
At its core, H-Orn(Tfa)-OH is ornithine, a non-essential amino acid. Ornithine has a five-carbon chain with an alpha-amino group and a carboxyl group. What distinguishes H-Orn(Tfa)-OH is the modification at the delta-amino group (the amino group on the fifth carbon) with a trifluoroacetyl (TFA) group. The chemical formula is C7H11F3N2O3, and its molecular weight is approximately 228.17 g/mol. The trifluoroacetyl group (-COCF3) is a common protecting group in organic synthesis due to its stability and the ease with which it can be removed under specific acidic conditions.
The synthesis of H-Orn(Tfa)-OH typically involves the selective acylation of the delta-amino group of ornithine. This is often achieved using trifluoroacetic anhydride or a similar trifluoroacetylating agent in the presence of a base or under controlled solvent conditions. Protecting the delta-amino group is crucial because ornithine has two amino groups, and selective reactions are often required in peptide synthesis or the construction of more complex molecules. The alpha-amino group and the carboxyl group remain available for subsequent reactions after the delta-amino group is protected.
The resulting H-Orn(Tfa)-OH is a versatile building block. Its structure allows it to be incorporated into peptide chains, serve as an intermediate in the synthesis of heterocyclic compounds, or be used in various organic transformations where a protected ornithine moiety is beneficial. The presence of the fluorine atoms in the TFA group can also influence the physical properties and reactivity of the molecule, making it unique compared to other protected amino acids.
For researchers and chemical manufacturers, reliable synthesis routes and high-purity products are essential. NINGBO INNO PHARMCHEM CO.,LTD., as a China-based supplier, ensures that H-Orn(Tfa)-OH is synthesized with precision, meeting the demanding specifications required for advanced chemical applications. Understanding the synthesis and structure of such compounds is fundamental to pushing the boundaries of chemical innovation.
Perspectives & Insights
Molecule Vision 7
“The synthesis of H-Orn(Tfa)-OH typically involves the selective acylation of the delta-amino group of ornithine.”
Alpha Origin 24
“This is often achieved using trifluoroacetic anhydride or a similar trifluoroacetylating agent in the presence of a base or under controlled solvent conditions.”
Future Analyst X
“Protecting the delta-amino group is crucial because ornithine has two amino groups, and selective reactions are often required in peptide synthesis or the construction of more complex molecules.”