Boc-Trp-OH - ≥98% , CAS No.13139-14-5

CAS: 13139-14-5 Cat. No.: B111757 Formula: C₁₆H₂₀N₂O₄ Molecular Weight: 304.34 Beilstein Registry Number: 39677 EC Number: 236-072-7

GRADE & PURITY ≥98%

Synonyms

AS-12736 | Boc-trytophan | CHEBI:183830 | tert-Butoxycarbonyltryptophan | L-Tryptophan, N-((1,1-dimethylethoxy)carbonyl)- | Nalpha-t-butoxycarbonyl-L-tryptophan | N-(tert-Butoxycarbonyl)-L-tryptophan | 2-(2-Fluorophenoxy)acetic | BOC-L-TRYPTOPHANE | EINEC

Storage

Room temperature,Argon charged

Shipped In

Normal

Specifications

Synonyms

AS-12736 | Boc-trytophan | CHEBI:183830 | tert-Butoxycarbonyltryptophan | L-Tryptophan, N-((1,1-dimethylethoxy)carbonyl)- | Nalpha-t-butoxycarbonyl-L-tryptophan | N-(tert-Butoxycarbonyl)-L-tryptophan | 2-(2-Fluorophenoxy)acetic | BOC-L-TRYPTOPHANE | EINEC

Specifications & Purity

≥98%

Storage

Room temperature,Argon charged

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488186159
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186159
• Canonical Smiles: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• IUPAC Name: (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• InChIKey: NFVNYBJCJGKVQK-ZDUSSCGKSA-N
• INCHI: 1S/C16H20N2O4/c1-16(2,3)22-15(21)18-13(14(19)20)8-10-9-17-12-7-5-4-6-11(10)12/h4-7,9,13,17H,8H2,1-3H3,(H,18,21)(H,19,20)/t13-/m0/s1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O
• WGK Germany: 3
• Molecular Weight: 304.34
• Beilstein: 39677
• Reaxy-Rn: 493747
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=493747&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indolyl carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indolyl carboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolyl carboxylic acids and derivatives
• Alternative Parents: Alpha amino acids and derivatives 3-alkylindoles Substituted pyrroles Benzenoids Heteroaromatic compounds Carbamate esters Organic carbonic acids and derivatives Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolyl carboxylic acid derivative - Alpha-amino acid or derivatives - 3-alkylindole - Indole - Substituted pyrrole - Benzenoid - Pyrrole - Carbamic acid ester - Heteroaromatic compound - Carbonic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Azacycle - Organic oxide - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

Discover Target: MMP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

IDO1 Tchem Indoleamine 2,3-dioxygenase (6650 Activities)

Discover Target: IDO1

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POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

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Associated Targets(non-human)

Klebsiella pneumoniae (43867 Activities)

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Escherichia coli (133304 Activities)

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Staphylococcus (1598 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus niger (16508 Activities)

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Fusarium oxysporum (3998 Activities)

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Xanthomonas oryzae (286 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Air sensitive; Light sensitive
• Specific Rotation[α]: -17.5 ° (C=2, DMF)
• Flash Point(°F): 132.8 °F
• Flash Point(°C): 56 °C
• Melt Point(°C): 134-138°C
• Molecular Weight: 304.340 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 304.142 Da
• Monoisotopic Mass: 304.142 Da
• Topological Polar Surface Area: 91.400 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 419.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhanpeng Ren, Jianying Wang, Chenglong Xue, Minghua Deng, Haiyang Yu, Tianci Lin, Jiayuan Zheng, Rongxiang He, Xianbao Wang, Jinhua Li.  (2023)  Ultrahighly Sensitive and Selective Glutathione Sensor Based on Carbon Dot-Functionalized Solution-Gate Graphene Transistor.  ANALYTICAL CHEMISTRY,      [PMID:37971943] [10.1021/acs.analchem.3c03656]

2. Yufeng Shi, Yingying Li, Nan Wu, Yudan Wang, Lijia Liu, Yawen Liu, Xuan Yuan, Junqing Li.  (2025)  Preparation and Characterization of pH-Responsive Microspheres Based on Sodium Alginate and Polyether Amine: Loading and Release of Tryptophan-Derived Cationic Antimicrobials.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.4c04050]

3. Yanyao Wang, Chengcheng Zhao, Taohong He, Weipeng Zhao, Annela M. Seddon, Dave J. Adams, Honghui Yang.  (2025)  N-Terminal Hydrogen Bonding Initiates Morphology Transition from Flat to Twisted Ribbon in an Amphiphilic Dipeptide Gel.  BIOMACROMOLECULES,      [PMID:41102987] [10.1021/acs.biomac.5c01528]