Boc-Trp-OH

Base Information

• Chemical Name: Boc-Trp-OH
• CAS No.: 13139-14-5
• Deprecated CAS: 118552-56-0,259144-37-1,957765-97-8,2045394-30-5,2634813-69-5
• Molecular Formula: C16H20N2O4
• Molecular Weight: 304.346
• Hs Code.: 29339900
• European Community (EC) Number: 236-072-7
• DSSTox Substance ID: DTXSID20884506
• Nikkaji Number: J317.828E
• Wikidata: Q72510532
• ChEMBL ID: CHEMBL65709
• Mol file: 13139-14-5.mol

Synonyms:Boc-tryptophan;tert-butyloxycarbonyl-L-tryptophan;tert-butyloxycarbonyltryptophan;tert-butyloxycarbonyltryptophan, (D)-isomer

Chemical Property of Boc-Trp-OH

Chemical Property:

• Appearance/Colour: White to off-white granular powder
• Vapor Pressure: 2.63E-12mmHg at 25°C
• Melting Point: 136 °C (dec.)
• Refractive Index: -17.5 ° (C=2, DMF)
• Boiling Point: 535.7 °C at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 277.8 °C
• PSA: 91.42000
• Density: 1.262 g/cm³
• LogP: 3.07920
• Storage Temp.: −20°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 304.14230712
• Heavy Atom Count: 22
• Complexity: 419

Purity/Quality:

99% ^*data from raw suppliers

Nα-Boc-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O
• Uses: Nα-Boc-L-tryptophan is an N-Boc-protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.

Technology Process of Boc-Trp-OH

There total 47 articles about Boc-Trp-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Boc-Trp-OH (13139-14-5)

Guidance literature:

With triethylamine; In methanol; at 0 ℃; for 15h;

DOI:10.1016/S0040-4020(01)01044-4

Reference yield: 100.0%

C30H30N2O5 → Boc-Trp-OH (13139-14-5)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1021/acscatal.7b02117

Reference yield: 100.0%

(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester (182949-67-3) → Boc-Trp-OH (13139-14-5)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 2h; Irradiation;

DOI:10.1021/acscatal.7b02117

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

L-Tryptophan

di-tert-butyl dicarbonate

Fmoc-Trp-OH

Downstream raw materials:

2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate

(tert-butyloxycarbonyl)-l-tryptophan p-nitrophenyl ester

N-tert-butoxycarbonyl-L-tryptophan-L-leucine methylester

N-α-boc-L-tryptophan 3,5-dimethylbenzyl ester

Refernces

• 1、 Xiao, Jinchong,Xu, Jialiang,Cui, Shuang,Liu, Huibiao,Wang, Shu,Li, Yuliang. "Supramolecular helix of an amphiphilic pyrene derivative induced by chiral tryptophan through electrostatic interactions". . p. 645 - 648. Retrieved 2008.
• 2、 Li, Xiaoyang,Wu, Jingde,Li, Xiaoguang,Mu, Weiwei,Liu, Xueliang,Jin, Yiming,Xu, Wenfang,Zhang, Yingjie. "Development of N-hydroxybenzamide derivatives with indole-containing cap group as histone deacetylases inhibitors". . p. 6258 - 6270. Retrieved 2015.
• 3、 Bernatowicz, Michael S.,Chao, Hann-Guang,Matsueda, Gary R.. "The (+/-)-1-(4-Methoxyphenyl)ethyl Ester as a Carboxyl Protecting Group". . p. 1651 - 1652. Retrieved 1994.
• 4、 Shivamallu, Chandan,Sharanaiah, Umesha,Kollur, Shiva Prasad,Mallesh, Naveen Kumar R.,Hosakere, Revanasiddappa D.,Balamurugan. "Pseudo-peptides as novel antileptospiral agents: Synthesis and spectral characterization". . p. 1152 - 1157. Retrieved 2014.
• 5、 Xu, Kuo-Xi,He, Yong-Bing,Qin, Hai-Juan,Qing, Guang-Yan,Liu, Shun-Ying. "Enantioselective recognition by optically active chiral fluorescence sensors bearing amino acid units". . p. 3042 - 3048. Retrieved 2005.
• 6、 Tammler, Ursula,Quillan, J. Mark,Lehmann, Jochen,Sadee, Wolfgang,Kassack, Matthias U.. "Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor". . p. 481 - 493. Retrieved 2003.
• 7、 Yokoyama,Hikawa,Murakami. "Does water suppress the racemization and decomposition of amino acids?". . p. 1431 - 1434. Retrieved 2001.
• 8、 Cockram, Peter E.,Slawin, Alexandra M. Z.,Smith, Terry K.,Turner, Callum A.. "Convenient Synthesis of Alternatively Bridged Tryptophan Ketopiperazines and Their Activities against Trypanosomatid Parasites". supporting information. . Retrieved 2022/01/11.