N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester
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N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester

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Boc-L-thiocitrulline tert-Butyl Ester is an analogue of L-thiocitrulline as an inhibitor of the isoforms of nitric oxide synthase (NOS).

Category
BOC-Amino Acids
Catalog number
BAT-003139
CAS number
133565-49-8
Molecular Formula
C15H29N3O4S
Molecular Weight
347.48
N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester
IUPAC Name
tert-butyl (2S)-5-(carbamothioylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
Synonyms
Boc-ThioCit-OtBu; tert-butyl(2S)-5-(carbamothioylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate; Boc-L-thiocitrulline t-butyl ester
Purity
≥ 95%
Storage
Store at -20 °C
InChI
InChI=1S/C15H29N3O4S/c1-14(2,3)21-11(19)10(8-7-9-17-12(16)23)18-13(20)22-15(4,5)6/h10H,7-9H2,1-6H3,(H,18,20)(H3,16,17,23)/t10-/m0/s1
InChI Key
BZCHKHCGOVKYIY-JTQLQIEISA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CCCNC(=S)N)NC(=O)OC(C)(C)C

N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester is a complex chemical compound, primarily recognized for its role as a precursor or intermediate in the synthesis of other pharmacologically relevant molecules. It is characterized by its unique chemical structure, which includes a thiocitrulline moiety combined with protective t-butoxycarbonyl (Boc) and t-butyl ester groups. This structure provides it with specific physicochemical properties that make it suitable for various applications, especially in medicinal chemistry and drug design. The compound’s protective groups are particularly crucial for preventing premature reactions during synthesis, facilitating the creation of more complex molecules with desired functionalities.

One key application of N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester is in peptide synthesis. Peptides are chains of amino acids that serve as fundamental building blocks for proteins. The protective groups in this compound are instrumental in sequential peptide synthesis, providing stability and preventing side reactions. This compound can be selectively deprotected when required, allowing for precise incorporation into peptide chains. Such a capability is critical in the development of peptide-based therapeutics, where maintaining structural fidelity during synthesis is paramount to ensure efficacy and safety in pharmaceutical applications.

Another significant application is in the field of enzyme inhibition studies. N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester can be used as an inhibitor in nitric oxide synthase (NOS) research. NOS is an enzyme responsible for the production of nitric oxide, a signaling molecule involved in numerous physiological processes. By studying the inhibitory effects of this compound, researchers can gain insights into the regulation of NOS activity, potentially leading to therapeutic applications in diseases where nitric oxide levels are dysregulated, such as in cardiovascular diseases and certain neurodegenerative disorders.

In addition, this compound finds application in medicinal chemistry research, particularly in the design of novel drug candidates. Its unique structure can be employed to create derivatives with potential therapeutic benefits. The ability to easily modify or replace its functional groups makes it a versatile scaffold in drug development. Medicinal chemists exploit this versatility to explore new chemical spaces, optimizing pharmacokinetic and pharmacodynamic properties to identify promising lead compounds for further development. This adaptability makes it a valuable tool in the continuous search for innovative treatments across various medical fields.

Lastly, N-α-(t-Butoxycarbonyl)-L-thiocitrulline t-butyl ester is utilized in chemical biology to explore cellular processes. By serving as a building block in the construction of molecular probes, researchers can label and track interactions and transformations within live cells, offering insights into complex biological pathways. These probes can help elucidate the roles of specific proteins or enzymes in health and disease, providing foundational knowledge that can drive the development of targeted therapies. As such, this compound is essential in the toolkit of chemical biologists working to decode the intricate web of life at the molecular level.

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