N-((5-(Dimethylamino)-1-naphthalenyl)sulfonyl)-L-tryptophan

Base Information

• Chemical Name: N-((5-(Dimethylamino)-1-naphthalenyl)sulfonyl)-L-tryptophan
• CAS No.: 19461-29-1
• Molecular Formula: C₂₃H₂₃N₃O₄S
• Molecular Weight: 437.519
• DSSTox Substance ID: DTXSID30941210
• Nikkaji Number: J293.372A
• Mol file: 19461-29-1.mol

Synonyms:19461-29-1;DNS-tryptophan;Dansyl-L-tryptophan;N-((5-(Dimethylamino)-1-naphthalenyl)sulfonyl)-L-tryptophan;L-Tryptophan, N-((5-(dimethylamino)-1-naphthalenyl)sulfonyl)-;(2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-(1H-indol-3-yl)propanoic acid;N-Alpha-dansyl-L-tryptophan cyclohexylammonium salt;Nalpha-Dansyl-L-tryptophan cyclohexylammonium salt;dansyl-tryptophan;SCHEMBL4133797;DTXSID30941210;AKOS015916029;N-[5-(Dimethylamino)naphthalene-1-sulfonyl]tryptophan;(S)-2-(5-(dimethylamino)naphthalene-1-sulfonamido)-3-(1H-indol-3-yl)propanoic acid

Chemical Property of N-((5-(Dimethylamino)-1-naphthalenyl)sulfonyl)-L-tryptophan

Chemical Property:

• Vapor Pressure: 1.91E-20mmHg at 25°C
• Boiling Point: 697.9°C at 760 mmHg
• PKA: 3.29±0.10(Predicted)
• Flash Point: 375.9°C
• PSA: 110.88000
• Density: 1.396g/cm³
• LogP: 4.83300
• Storage Temp.: −20°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 437.14092740
• Heavy Atom Count: 31
• Complexity: 738

Purity/Quality:

97% ^*data from raw suppliers

N-ALPHA-DANSYL-L-TRYPTOPHAN CYCLOHEXYLAMMONIUM SALT 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C1=CC=CC2=C1C=CC=C2S(=O)(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O
• Isomeric SMILES: CN(C)C1=CC=CC2=C1C=CC=C2S(=O)(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O

Technology Process of N-((5-(Dimethylamino)-1-naphthalenyl)sulfonyl)-L-tryptophan

There total 3 articles about N-((5-(Dimethylamino)-1-naphthalenyl)sulfonyl)-L-tryptophan 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: 40.0%

dansyl-L-tryptophan methyl ester (108353-30-6) → L-dansyltryptophan (19461-29-1)

Guidance literature:

With water; sodium hydroxide; at 45 ℃; for 12h;

DOI:10.1039/b907386h

Reference yield:

dansyl-D,L-tryptophan (17039-57-5) → L-dansyltryptophan (19461-29-1) + Dns-D-Trp

Guidance literature:

DOI:10.1021/ac950698c

Reference yield:

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) + Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → L-dansyltryptophan (19461-29-1) + Dns-D-Trp

Guidance literature:

Multi-step reaction with 2 steps

1: lithium carbonate / acetone / 0.5 h / 20 °C

2: boric acid; β‐cyclodextrin; zinc(II) sulfate; L-leucine; ammonium acetate / aq. buffer / 25 °C / pH 8.2 / Resolution of racemate

With L-leucine; ammonium acetate; boric acid; lithium carbonate; zinc(II) sulfate; β‐cyclodextrin; In acetone;

DOI:10.1039/c4ra09433f

upstream raw materials:

dansyl-D,L-tryptophan

dansyl-L-tryptophan methyl ester

5-(dimethylamino)naphth-1-ylsulfonyl chloride

Trp

Refernces

• 1、 Su, Yuan,Mu, Xiaoyu,Qi, Li. "A new chiral ligand exchange capillary electrophoresis system based on Zn(ii)-l-leucine complexes coordinating with β-cyclodextrin and its application in screening tyrosinase inhibitors". . p. 55280 - 55285. Retrieved 2015/02/05.
• 2、 Messina,Girelli,Flieger,Sinibaldi,Sedmera,Cvak. "Direct resolution of optically active isomers on chiral packings containing ergoline skeletons. 5. Enantioseparation of amino acid derivatives". . p. 1191 - 1196. Retrieved 2007/10/03.