CAS 133174-15-9

N(alpha)-fmoc-L-citrulline

Description:

N(alpha)-Fmoc-L-citrulline is a derivative of the amino acid citrulline, characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protective group at the alpha-amino position. This modification enhances its stability and solubility, making it suitable for use in peptide synthesis and other biochemical applications. The Fmoc group is commonly used in solid-phase peptide synthesis due to its ease of removal under mild basic conditions. L-citrulline itself is a non-proteinogenic amino acid that plays a role in the urea cycle and is involved in nitric oxide production, contributing to various physiological processes. N(alpha)-Fmoc-L-citrulline is typically utilized in research and pharmaceutical contexts, particularly in the development of peptides and proteins with specific functional properties. Its molecular structure includes a side chain that contains a guanidinium group, which can influence the compound's interactions and reactivity in biological systems. Overall, N(alpha)-Fmoc-L-citrulline serves as a valuable building block in peptide chemistry and biochemistry.

Formula: C₂₁H₂₃N₃O₅

InChI: InChI=1/C21H23N3O5/c22-20(27)23-11-5-10-18(19(25)26)24-21(28)29-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,24,28)(H,25,26)(H3,22,23,27)/t18-/m0/s1

SMILES: c1ccc2c(c1)c1ccccc1C2COC(=N[C@@H](CCCNC(=N)O)C(=O)O)O

Synonyms:

• Fmoc-L-citrulline
• Fmoc-Cit-OH
• N~5~-carbamoyl-N~2~-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-ornithine

Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-citrulline

CAS: 133174-15-9

Formula: C₂₁H₂₃N₃O₅

Purity: >98.0%(T)(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 397.43

Ref: 3B-F0626

N-Fmoc-L-citrulline, 98%

CAS: 133174-15-9

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Formula: C₂₁H₂₃N₃O₅

Purity: 98%

Color and Shape: Solid, White to off-white

Molecular weight: 397.43

Ref: 02-H63342

Fmoc-Cit-OH

CAS: 133174-15-9

Bachem ID: 4017699.

Formula: C₂₁H₂₃N₃O₅

Purity: 99.0%

Color and Shape: White Powder

Molecular weight: 397.43

Ref: 01-4017699

L-Ornithine, N5-(aminocarbonyl)-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-

CAS: 133174-15-9

Formula: C₂₁H₂₃N₃O₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 397.4244

Ref: IN-DA0014DK

Fmoc-Cit-OH

CAS: 133174-15-9

Molecular weight: 397.42

Ref: 7W-GM0513

Fmoc-L-Citrulline

CAS: 133174-15-9

Fmoc-L-Citrulline

Purity: 98%

Molecular weight: 397.42g/mol

Ref: 54-OR1013368

Fmoc-Cit-OH

CAS: 133174-15-9

M03232 - Fmoc-Cit-OH

Formula: C₂₁H₂₃N₃O₅

Purity: 97%

Color and Shape: Solid, Crystalline Powder

Molecular weight: 397.431

Ref: 10-M03232

FMOC-L-Citrulline extrapure, 99%

CAS: 133174-15-9

Formula: C₂₁H₂₃N₃O₅

Purity: min. 99%

Color and Shape: White to off white to slight yellow to beige, Crystalline powder

Molecular weight: 397.43

Ref: SR-61458

Fmoc-Cit-OH

CAS: 133174-15-9

Fmoc-Cit-OH, or N-Fmoc-L-citrulline, is a protected amino acid derivative commonly used in peptide synthesis. The "Fmoc" portion refers to the fluorenylmethyloxycarbonyl group, a protecting group that shields the amino group of citrulline, preventing unwanted side reactions during peptide chain elongation. Citrulline, the core amino acid in Fmoc-Cit-OH, is a non-proteinogenic amino acid, which is not directly incorporated into proteins during translation. In peptide synthesis, Fmoc-Cit-OH is incorporated into peptide chains using solid-phase peptide synthesis (SPPS). This technique allows for the stepwise assembly of peptides on a solid support, with Fmoc-protected amino acids added sequentially. The Fmoc group is then removed using a mild base, exposing the free amino group for the addition of the next amino acid. Fmoc-Cit-OH is particularly valuable in the synthesis of peptides containing citrulline residues, which are often found in biologically active peptides and proteins. These peptides may have therapeutic potential in various fields, including drug discovery and prodrug synthesis.

Formula: C₂₁H₂₃N₃O₅

Purity: Min. 98 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 397.42 g/mol

Ref: 3D-FF10665