Fmoc-selenocysteine(trityl)-OH
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Fmoc-selenocysteine(trityl)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008544
CAS number
1639843-37-0
Molecular Formula
C37H31NO4Se
Molecular Weight
632.6
IUPAC Name
2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylselanylpropanoic acid
Alternative CAS
2044709-97-7
Synonyms
Fmoc-DL-Sec(Trt)-OH
Boiling Point
798.1±60.0 °C at 760 mmHg
InChI
InChI=1S/C37H31NO4Se/c39-35(40)34(38-36(41)42-24-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)25-43-37(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34H,24-25H2,(H,38,41)(H,39,40)/t34-/m0/s1
InChI Key
BNOGRCVLEKLKJK-UMSFTDKQSA-N
Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)[Se]CC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-selenocysteine(trityl)-OH, a derivative of the amino acid selenocysteine shielded by Fmoc and trityl groups, finds extensive applications in synthetic chemistry and biochemistry. Explore the diverse realms of Fmoc-selenocysteine(trityl)-OH through the lens of high perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in selenopeptide synthesis, Fmoc-selenocysteine(trityl)-OH enables the incorporation of selenocysteine into peptide structures. This distinctive amino acid, often heralded as the 21st amino acid, possesses catalytic properties that set it apart. Its utilization opens pathways for studying selenium-enriched enzymes and proteins, shedding light on intricate biochemical processes.

Protein Engineering: Within the domain of protein engineering, Fmoc-selenocysteine(trityl)-OH emerges as a pivotal tool for integrating selenocysteines into protein frameworks. This integration gives rise to novel proteins endowed with enhanced functionalities. Engineered proteins may showcase heightened catalytic efficiency or stability compared to their natural counterparts, fueling advancements in biocatalysis and therapeutic protein design.

Bioorthogonal Chemistry: Delving into the realm of bioorthogonal chemistry, Fmoc-selenocysteine(trityl)-OH plays a vital role in labeling and modifying proteins within live-cell environments. The distinct reactivity of selenocysteine allows for precise and effective bioconjugation reactions. This technique stands as a valuable asset for real-time exploration of protein dynamics and interactions within living cells, unlocking new dimensions in biochemical research.

Redox Biology Research: The intricate interplay of selenocysteine in redox biology unfolds with the aid of Fmoc-selenocysteine(trityl)-OH, facilitating the synthesis of proteins involved in redox processes. By incorporating selenocysteine, researchers delve into the functionality of selenoproteins, pivotal players in antioxidant defense and redox modulation. This exploration deepens our comprehension of oxidative stress-related diseases and aids in crafting novel therapeutic interventions.

1. Diversity of N-triphenylacetyl-L-tyrosine solvates with halogenated solvents
Agnieszka Czapik, Marcin Kwit Acta Crystallogr C Struct Chem. 2021 Dec 1;77(Pt 12):745-756. doi: 10.1107/S2053229621011098. Epub 2021 Nov 5.
The structure of N-triphenylacetyl-L-tyrosine (C29H25NO4, L-TrCOTyr) is characterized by the presence of both donors and acceptors of classical hydrogen bonds. At the same time, the molecule contains a sterically demanding and hydrophobic trityl group capable of participating in π-electron interactions. Due to its large volume, the trityl group may favour the formation of structural voids in the crystals, which can be filled with guest molecules. In this article, we present the crystal structures of a series of N-triphenylacetyl-L-tyrosine solvates with chloroform, namely, L-TrCOTyr·CHCl3 (I) and L-TrCOTyr·1.5CHCl3 (III), and dichloromethane, namely, L-TrCOTyr·CH2Cl2 (II) and L-TrCOTyr·0.1CH2Cl2 (IV). To complement the topic, we also decided to use the racemic amide N-triphenylacetyl-DL-tyrosine (rac-TrCOTyr) and recrystallized it from a mixture of chloroform and dichloromethane. As a result, rac-TrCOTyr·1.5CHCl3 (V) was obtained. In the crystal structures, the amide molecules interact with each other via O-H...O hydrogen bonds. Noticeably, the amide N-H group does not participate in the formation of intermolecular hydrogen bonds. Channels are formed between the TrCOTyr molecules and these are filled with solvent molecules. Additionally, in the crystals of III and V, there are structural voids that are occupied by chloroform molecules. Structure analysis has shown that solvates I and II are isostructural. Upon loss of solvent, the solvates transform into the solvent-free form of TrCOTyr, as confirmed by thermogravimetric analysis, differential scanning calorimetry and powder X-ray diffraction.
2. 1-trityl-4-nitroimidazole
E Skrzypczak-Jankun, R G Kurumbail Acta Crystallogr C. 1996 Jan 15;52 ( Pt 1):189-91. doi: 10.1107/s0108270195010183.
X-ray analysis confirmed the configuration of the title N1-alkylated C4-nitroimidazole inhibitor. The plane of the imidazole ring, sitting on an axis of the trityl propeller, bisects the angle between two phenyl rings, while the nitro group extends over the third. Modeling of the interactions between the cytochrome P450 and the title compound (C22H17N3O2) has been performed on the basis of the crystal structures of 1-trityl-4-nitroimidazole and bacterial cytochrome P450BM-3. The replacements and deletions in the sequence of the latter has been performed to match mammalian cytochrome P450-IIIA1. The modeling explained why inhibitors with a C4-substituted imidazole ring showed lower effectivity than those without substituents, as an additional group of atoms at C4 prevents close interactions of the imidazole ring with the heme Fe atom.
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