N-α-Boc-N-in-Boc-L-tryptophan is a protected tryptophan derivative in which the amino acid backbone is modified with an N-α Boc group and the indole nitrogen is additionally protected as a Boc carbamate (N-in-Boc), maintaining the tryptophan side chain featuring an indole ring. The molecule contains a carboxyl functional group (typically present as the free acid or a protected acid form depending on the supplied material) alongside two Boc-protected nitrogen sites that suppress undesired amine reactivity and provide controlled chemoselectivity during peptide-coupling steps. N-α-Boc-N-in-Boc-L-tryptophan is used as a building block for peptide synthesis and for preparing tryptophan-containing peptide or conjugate intermediates where temporary protection of both the α-amino group and the indole nitrogen supports stepwise assembly and downstream deprotection strategies.
CAT No: CP02011
CAS No:144599-95-1
Synonyms/Alias:Boc-Trp(Boc)-OH;144599-95-1;(S)-3-(1-(tert-Butoxycarbonyl)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoicacid;Boc-L-Trp(Boc)-OH;AmbotzBAA1140;AC1ODSVN;BOC-TRP-OH;SCHEMBL10310207;CTK8F0154;MolPort-008-267-375;ACT09489;ZINC2562519;CB-941;AKOS022175632;DS-3075;AJ-40772;AK144695;BP-21161;RT-011778;ST2408317;FT-0657175;V3341;K-4636;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoicacid
N-α-Boc-N-in-Boc-L-tryptophan is a protected L-tryptophan derivative in which the indole-bearing amino acid framework is rendered as a doubly Boc-protected system, featuring an Nα-Boc group and an additional N-in-Boc protection pattern that masks the indole-related nitrogen functionality. The molecule therefore presents a chiral amino acid core with the stereogenic center retained from L-tryptophan, while the indole ring remains present for downstream electrophilic substitution, cyclization, or conjugation chemistry under appropriate conditions. Boc carbamate groups introduce controlled deprotection behavior compatible with peptide synthesis workflows, enabling stepwise unveiling of reactive amine functionality without exposing the indole nitrogen prematurely. The resulting reactivity profile supports use as a protected amino acid intermediate and peptide building block precursor for constructing tryptophan-containing sequences and for preparing chiral, nitrogen-functionalized indole derivatives for synthetic and biochemical research.
1. Peptide Synthesis
N-α-Boc-N-in-Boc-L-tryptophan is applied in peptide synthesis as a protected tryptophan building block where orthogonal Boc-type carbamate protection helps manage chemoselectivity during coupling and subsequent deprotection cycles. The chiral amino acid backbone provides a stereodefined residue for amide bond formation, while the indole-containing side chain supports incorporation into peptides intended for receptor-binding studies, folding investigations, or membrane-associated sequence design. Boc masking strategies can be leveraged to control exposure of the amino functionality during stepwise assembly, supporting sequential N-terminal and side-chain transformation planning in solid-phase or solution-phase workflows. Downstream peptide analogs derived from this residue can be used to probe sequence-dependent properties and to generate tryptophan-rich scaffolds for chemical biology and materials-oriented peptide engineering.
2. Unnatural Amino Acid Incorporation
N-α-Boc-N-in-Boc-L-tryptophan is suitable for unnatural amino acid incorporation and scaffold diversification because the protected indole nitrogen and carbamate-protected amine enable controlled derivatization before or after peptide assembly. The stereogenic L-tryptophan center provides a defined chiral stereochemical handle, while the indole ring can participate in further functional group installation such as N-alkylation, electrophilic substitution, or tethering to electrophiles under conditions that respect Boc stability. Boc-based protection supports a strategy where the amino acid is handled as a stable intermediate during synthesis, then converted into a reactive coupling partner or a selectively unmasked residue for incorporation into peptides and peptidomimetics. Resulting derivatives can serve as chiral building blocks for mapping side-chain effects on binding, conformational behavior, and molecular recognition in structure-activity relationship studies.
3. Bioconjugation Chemistry
N-α-Boc-N-in-Boc-L-tryptophan is used in bioconjugation chemistry and chemical biology workflows where protected tryptophan derivatives act as precursors to indole-functionalized linkers and conjugation-ready intermediates. The protected amino functionality and carbamate groups provide a means to regulate reactivity during linker synthesis, while the indole moiety can be transformed into conjugation handles for attachment to biomolecules such as proteins, peptides, or nucleic-acid-associated constructs. Boc deprotection planning enables stepwise generation of reactive amine or indole-derived electrophile/nucleophile forms that can be coupled to activated esters, aldehydes, or other functional groups on target biomolecules. Downstream conjugates can be employed for labeling, affinity reagent preparation, and analytical studies requiring chiral, tryptophan-based attachment points.
4. Process Chemistry Intermediate
N-α-Boc-N-in-Boc-L-tryptophan is relevant to process chemistry intermediate preparation for fine chemical and pharmaceutical-intermediate supply chains that require stable, isolable protected amino acid forms. The dual Boc protection pattern improves handling stability by suppressing premature amine reactivity, while the defined L-configuration supports consistent stereochemical outcomes across multi-step manufacturing routes. Carbamate protection also enables predictable deprotection logic, allowing manufacturing teams to design sequences where orthogonal unmasking steps yield targeted coupling partners or downstream indole-modified intermediates. The compound's protected amino acid structure supports scale-up-oriented synthesis planning for tryptophan-containing intermediates used in peptide-manufacturing workflows and in the preparation of chiral indole derivatives for specialty chemical production.
5. Peptidomimetics And SAR Studies
N-α-Boc-N-in-Boc-L-tryptophan is applied in peptidomimetics and structure-activity relationship studies where tryptophan-derived chiral fragments are incorporated into non-native backbones or side-chain-modified analogs. The indole-bearing side chain provides an aromatic, nitrogen-containing motif that can be retained, functionalized, or used as a scaffold for further ring substitution, while the protected amino groups support controlled transformation into coupling-ready forms. Boc-based protection strategies allow chemists to manage stepwise assembly of analogs, including the preparation of N-terminally defined fragments and the generation of selectively deprotected intermediates for analog diversification. Resulting peptidomimetic libraries and SAR-focused analog sets benefit from the stereochemical fidelity of the L-tryptophan core and from the ability to tune indole reactivity through downstream derivatization chemistry.
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