N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-leucine 1,1-dimethylethyl ester

Base Information

• Chemical Name: N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-leucine 1,1-dimethylethyl ester
• CAS No.: 27167-65-3
• Molecular Formula: C₂₁H₃₂N₂O₅
• Molecular Weight: 392.495
• DSSTox Substance ID: DTXSID601154113
• Mol file: 27167-65-3.mol

Synonyms:SCHEMBL7607055;NLGQUDIPPKUHPX-RDJZCZTQSA-N;DTXSID601154113;N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-leucine 1,1-dimethylethyl ester;(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-4-methyl-pentanoic acid tert-butyl ester;27167-65-3

Chemical Property of N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-leucine 1,1-dimethylethyl ester

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 392.23112213
• Heavy Atom Count: 28
• Complexity: 521

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC(C(=O)OC(C)(C)C)NC(=O)C(C)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1

Technology Process of N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-leucine 1,1-dimethylethyl ester

There total 9 articles about N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-leucine 1,1-dimethylethyl ester 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: 91.0%

L-leucine tert-butyl ester (21691-53-2) + Z-L-Ala 2,2,2-trifluoroethyl ester (203640-41-9) → (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-4-methylpentanoate (27167-65-3)

Guidance literature:

With cross-linked enzyme aggregate of Alcalase; at 50 ℃; for 16h; Molecular sieve; Enzymatic reaction;

DOI:10.1016/j.molcatb.2011.03.012

Reference yield: 85.0%

L-leucine tert-butyl ester (21691-53-2) + (S)-2-benzyloxycarbonylamino-propionic acid methyl ester (28819-05-8) → (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-4-methylpentanoate (27167-65-3)

Guidance literature:

With cross-linked enzyme aggregates of Alcalase; at 50 ℃; for 20h; Molecular sieve; Enzymatic reaction;

DOI:10.1002/adsc.201000313

Reference yield: 78.0%

L-leucine tert-butyl ester (21691-53-2) + Z-L-Ala carbamoylmethyl ester (4816-87-9) → (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)-4-methylpentanoate (27167-65-3)

Guidance literature:

With phosphate buffer; mercaptoacetic acid; In ethyl acetate; for 0.166667h; Ambient temperature; papain;

DOI:10.1007/BF00811332

upstream raw materials:

L-leucine tert-butyl ester

N-Cbz-Ala

L-leucine tert-butyl ester hydrochloride

(N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester

Downstream raw materials:

N-carbobenzoxy-L-alanyl-L-leucine methyl ester

H-Gly-L-Ala-L-Leu-OH

N-2-Phenyl-iso-propyloxycarbonyl-S-ethylthio-cysteinyl-alanyl-leucin-tert.-butylester

(S)-tert-butyl 2-((S)-2-aminopropanamido)-4-methylpentanoate

Refernces

• 1、 Nuijens, Timo,Cusan, Claudia,Schepers, Annette C.H.M.,Kruijtzer, John A.W.,Rijkers, Dirk T.S.,Liskamp, Rob M.J.,Quaedflieg, Peter J.L.M.. "Enzymatic synthesis of activated esters and their subsequent use in enzyme-based peptide synthesis". . p. 79 - 84. Retrieved 2012/02/03.
• 2、 Wartchow, Charles A.,Wang, Peng,Bednarski, Mark D.,Callstrom, Matthew R.. "Carbohydrate Protease Conjugates: Stabilized Proteases for Peptide Synthesis". . p. 2216 - 2226. Retrieved 2007/10/02.