Z-Ala-OSu

Base Information

• Chemical Name: Z-Ala-OSu
• CAS No.: 3401-36-3
• Molecular Formula: C15H16N2O6
• Molecular Weight: 320.302
• Hs Code.: 29280000
• DSSTox Substance ID: DTXSID10356929
• Nikkaji Number: J977.394K
• Wikidata: Q72441858
• Mol file: 3401-36-3.mol

Synonyms:Z-Ala-OSu;3401-36-3;(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)propanoate;l-alanine,n-((phenylmethoxy)carbonyl)-,2,5-dioxo-1-pyrrolidinyl ester;L-Alanine,N-[(phenylmethoxy)carbonyl]-,2,5-dioxo-1-pyrrolidinyl ester;Z-L-alanine hydroxysuccinimide ester;SCHEMBL4432276;L-Alanine, N-[(phenylmethoxy)carbonyl]-, 2,5-dioxo-1-pyrrolidinyl ester;DTXSID10356929;CS-M1504;MFCD00053548;AKOS016002991;FD21112;AS-10247;HY-77132;A851147;N-(Benzyloxycarbonyl)-L-alanine succinimidyl ester;2,5-Dioxo-1-pyrrolidinyl N-[(benzyloxy)carbonyl]alaninate;2,5-Dioxopyrrolidin-1-yl ((benzyloxy)carbonyl)-L-alaninate;N-CARBOBENZOXY-L-ALANINE-N-HYDROXYSUCCINIMIDE ESTER;N^a-Benzyloxycarbonyl-L-alanine N-succinimidyl ester, 97%

Chemical Property of Z-Ala-OSu

Chemical Property:

• Melting Point: 119-123 °C
• Refractive Index: 1.579
• PSA: 102.01000
• Density: 1.36 g/cm³
• LogP: 1.23730
• Storage Temp.: −20°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 320.10083623
• Heavy Atom Count: 23
• Complexity: 470

Purity/Quality:

99% ^*data from raw suppliers

Z-L-alanine-N-hydroxysuccinimide ester ^*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: CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C[C@@H](C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2=CC=CC=C2

Technology Process of Z-Ala-OSu

There total 11 articles about Z-Ala-OSu 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: 95.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-Cbz-Ala (1142-20-7) → (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester (3401-36-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; at 0 ℃;

Reference yield: 94.0%

N-Cbz-Ala (1142-20-7) + bis(N-hydroxysuccinimide) sulfite (90704-86-2) → (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester (3401-36-3)

Guidance literature:

With pyridine; In acetonitrile; at 20 ℃; for 1.5h; further solvent, base;

DOI:10.1007/BF01141728

Reference yield: 87.0%

N-Cbz-Ala (1142-20-7) + N-hydroxysuccinimido diphenyl phosphate (75513-55-2) → (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester (3401-36-3)

Guidance literature:

With triethylamine;

DOI:10.1016/S0040-4039(00)92747-3

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-Cbz-Ala

N-hydroxysuccinimido diphenyl phosphate

N,N’-disuccinimidyl oxalate

Downstream raw materials:

N-benzyloxycarbonyl L-alanine acetoxime ester

[(N-benzyloxycarbonyl-L-alanyl)amino]-methylphosphonic acid

Cbz-L-Ala-D-Gln

1-R-1-[(N-benzyloxycarbonyl-L-alanyl)amino]ethanephosphonic acid

Refernces

• 1、 Escorihuela, Jorge,Burguete, M. Isabel,Ujaque, Gregori,Lledós, Agustí,Luis, Santiago V.. "Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands". supporting information. p. 11125 - 11136. Retrieved 2016/12/07.
• 2、 Hervé, Mireille,Kova?, Andreja,Cardoso, Cécile,Patin, Delphine,Brus, Boris,Barreteau, Hélène,Mengin-Lecreulx, Dominique,Gobec, Stanislav,Blanot, Didier. "Synthetic tripeptides as alternate substrates of murein peptide ligase (Mpl)". . p. 1120 - 1126. Retrieved 2013/07/05.