Boc-Thionoleu-1-(6-nitro)benzotriazolide is a Boc-protected amino acid derivative in which a thionoleucine-like amino acid scaffold is converted to a benzotriazolide activated carboxylate for peptide coupling. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality, while the carboxyl group is masked as a 1-(6-nitro)benzotriazolide leaving group, and the side chain bears a thioether-containing thionoleucine-type motif that can influence hydrophobicity and sulfur-based chemical behavior. In synthesis, this activated benzotriazolide form is employed as an intermediate to support stepwise formation of amide bonds during peptide assembly, including incorporation of the thionoleucine-like residue and introduction of the 6-nitrobenzotriazolide handle for controlled coupling under appropriate conditions.
CAT No: CP26783
CAS No:214750-70-6
Synonyms/Alias:Boc-ThionoLeu-1-(6-nitro)benzotriazolide;214750-70-6;PubChem10343;ZINC2244292;FT-0603892;(S)-2-(Boc-amino)-4-methyl-pentanethioicO-acid-1-(6-nitro)benzotriazolide
Boc-Thionoleu-1-(6-nitro)benzotriazolide is a Boc-protected thionoleucine-derived amino acid activation reagent featuring a chiral amino acid framework and a benzotriazolide leaving group bearing a 6-nitro substituent. The structure combines a tert-butoxycarbonyl (Boc) carbamate on the amino functionality with a thioamide/thionoleucine motif that can participate in acyl transfer chemistry, while the benzotriazolide moiety provides a stabilized anion pathway during peptide coupling. The presence of the nitro group on the benzotriazolide ring modulates electronic properties and can influence reactivity and compatibility with common coupling conditions. As a chiral amino acid derivative with a protected amine and an activated carboxyl equivalent, it is well suited as a peptide synthesis intermediate and as a controlled precursor for downstream functional group transformations in amino acid chemistry.
1. Peptide Coupling Reagents
Boc-Thionoleu-1-(6-nitro)benzotriazolide is used in peptide synthesis workflows where activated amino acid derivatives are required to form amide bonds under coupling conditions. The Boc-protected nitrogen and the benzotriazolide activation handle enable controlled conversion of the amino acid functionality into an acylating species while maintaining stereochemical integrity at the chiral center. The thionoleucine-derived reactive motif can participate in acyl transfer steps that support rapid incorporation into growing peptide chains, and the benzotriazolide leaving group supports efficient activation chemistry. The resulting peptide building block formation supports the construction of protected peptide fragments for subsequent deprotection and ligation strategies in research-grade peptide chemistry and fine chemical synthesis.
2. Protected Amino Acid Intermediates
Boc-Thionoleu-1-(6-nitro)benzotriazolide serves as a protected amino acid intermediate for synthesis planning that relies on orthogonal protecting-group strategies. The Boc carbamate provides a stable N-protection element that can be removed under standard deprotection regimes to reveal the amino group for further coupling or derivatization. The benzotriazolide portion functions as a transient activation group that can be leveraged to prepare C-terminal or side-chain modified derivatives without prematurely exposing reactive functionalities. The nitro-substituted benzotriazolide electronic environment can be exploited to tune reactivity profiles during intermediate preparation, supporting downstream conversion into Boc-protected thionoleucine-containing peptides and related amino acid derivatives.
3. Peptidomimetic And SAR Studies
Boc-Thionoleu-1-(6-nitro)benzotriazolide is applicable to peptidomimetic construction and structure-activity relationship studies where thionoleucine-like residues are incorporated to modulate backbone properties. The chiral amino acid scaffold and protected amine allow systematic generation of peptide analogs with controlled stereochemistry, while the thionoleucine motif can introduce altered hydrogen-bonding and conformational behavior compared with standard amino acids. The benzotriazolide activation chemistry enables stepwise assembly of analog series that maintain consistent protecting-group patterns across analog libraries. The resulting thionoleucine-containing peptide analogs can be used as chemical probes for SAR investigations and for mapping how side-chain and backbone modifications influence molecular recognition in biochemical research settings.
4. Chemical Manufacturing Intermediates
Boc-Thionoleu-1-(6-nitro)benzotriazolide is suitable for process chemistry intermediate preparation where activated amino acid reagents are manufactured and then consumed in downstream peptide or specialty chemical steps. The defined functional group set, including Boc-protected nitrogen and a benzotriazolide activation leaving group, supports reproducible handling as a discrete intermediate rather than an in situ generated activator. The nitro-substituted benzotriazolide ring provides a chemically distinct activation platform that can be integrated into manufacturing route design for thionoleucine-containing products and protected peptide fragments. The compound's role as a chiral, protected amino acid activation intermediate aligns with industrial fine chemical synthesis practices that require predictable coupling behavior and controlled downstream deprotection compatibility.
5. Analytical Standards For Amino Acid Chemistry
Boc-Thionoleu-1-(6-nitro)benzotriazolide can be employed in analytical research as a reference material for monitoring amino acid derivatization, activation efficiency, and protecting-group stability. The presence of the Boc carbamate, benzotriazolide activation moiety, and nitro substituent creates multiple chemically distinct signals that can support method development in LC-MS, HPLC, and related characterization workflows. The chiral amino acid framework enables stereochemical tracking when paired with chiral chromatography or stereospecific derivatization strategies. The compound's defined structure supports quantitative and qualitative assessment of intermediate conversion during protected amino acid synthesis and peptide building block preparation, contributing to reliable process development and synthetic method validation in applied amino acid chemistry.
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