Z-Ala-Trp-OH

Base Information

• Chemical Name: Z-Ala-Trp-OH
• CAS No.: 119645-65-7
• Molecular Formula: C22H23 N3 O5
• Molecular Weight: 409.442
• DSSTox Substance ID: DTXSID50426312
• Nikkaji Number: J2.111.054J
• ChEMBL ID: CHEMBL491109
• Mol file: 119645-65-7.mol

Synonyms:Z-Ala-Trp-OH;119645-65-7;(2S)-3-(1H-indol-3-yl)-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoic acid;Cbz-L-Ala-L-Trp;NSC-333447;MLS001243443;CHEMBL491109;SCHEMBL5380211;BDBM36237;DTXSID50426312;OEANOUHCLXZBNG-LIRRHRJNSA-N;HMS2211E14;MFCD00022761;AKOS024432241;AS-19611;SMR000841576;CARBOBENZYLOXY-L-ALANYL-L-TRYPTOPHAN;(S)-2-((S)-2-(benzyloxycarbonylamino)propanamido)-3-(1H-indol-3-yl)propanoic acid;(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-3-(1H-indol-3-yl)-propionic acid

Chemical Property of Z-Ala-Trp-OH

Chemical Property:

• Vapor Pressure: 3.88E-23mmHg at 25°C
• Refractive Index: 1.638
• Boiling Point: 742.3°C at 760 mmHg
• Flash Point: 402.7°C
• Density: 1.329g/cm³
• Storage Temp.: -15°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 409.16377084
• Heavy Atom Count: 30
• Complexity: 608

Purity/Quality:

98%min ^*data from raw suppliers

Z-Ala-Trp-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O)NC(=O)OCC3=CC=CC=C3

Technology Process of Z-Ala-Trp-OH

There total 4 articles about Z-Ala-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: 97.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate (820239-42-7) → (2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}propanoyl)amino]-3-(1H-indol-3-yl)propanoic acid (119645-65-7)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃;

DOI:10.1055/s-2004-831255

Reference yield:

Z-L-Ala-L-Trp-OMe (28944-98-1) → (2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}propanoyl)amino]-3-(1H-indol-3-yl)propanoic acid (119645-65-7)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water;

DOI:10.1016/j.ejmech.2021.113267

Reference yield:

C27H30N3O7Pol → (2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}propanoyl)amino]-3-(1H-indol-3-yl)propanoic acid (119645-65-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.333333h; Polystyrene

upstream raw materials:

L-Tryptophan

benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate

N-Cbz-Ala

Z-L-Ala-L-Trp-OMe

Downstream raw materials:

N^α-{[(benzyloxy)carbonyl]-L-alanyl}-1-{[(benzyloxy)carbonyl]-L-phenylalanyl}-L-tryptophan

Cbz-L-Ala-L-Trp-Bt

1-((S)-1-Benzyloxycarbonylamino-ethyl)-4,9-dihydro-3H-β-carboline-3-carboxylic acid

{(S)-1-[(S)-4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester

Refernces

• 1、 Liaqat, Sumaira,Panda, Siva S.,Rauf, Abdul,Al-Youbi, Abdulrahman O.,Katritzky, Alan R.. "Solution-phase synthesis of chiral N-, O-, and S-acyl isopeptides". . p. 67 - 72. Retrieved 2014/01/06.
• 2、 -. "Compounds for enzyme inhibition". Page/Page column 34-35. . Retrieved 2008/06/13.