N,N-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-L-glutaMic Acid 1-(1,1-DiMethylethyl) 5-(PhenylMethyl) Ester

Base Information

• Chemical Name: N,N-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-L-glutaMic Acid 1-(1,1-DiMethylethyl) 5-(PhenylMethyl) Ester
• CAS No.: 862778-54-9
• Molecular Formula: C₂₈H₄₃NO₈
• Molecular Weight: 521.651
• Mol file: 862778-54-9.mol

Synonyms:N,N-Bis[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-glutamic Acid 1-(1,1-Dimethylethyl) 5-(Phenylmethyl) Ester;

Chemical Property of N,N-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-L-glutaMic Acid 1-(1,1-DiMethylethyl) 5-(PhenylMethyl) Ester

Chemical Property:

• PSA: 108.44000
• LogP: 4.20570
• Solubility.: Chloroform, DCM, DMSO

Purity/Quality:

N,N-Bis[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-glutamicAcid1-(1,1-Dimethylethyl)5-(Phenylmethyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N,N-Bis[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-glutamic Acid 1-(1,1-Dimethylethyl) 5-(Phenylmethyl) Ester is an protected intermediate in the synthesis of chelating agent for fluorescence labeling of histidine-tagged proteins to lipid membranes, which is a powerful mean for studying and monitoring protein interaction in cells.

Technology Process of N,N-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-L-glutaMic Acid 1-(1,1-DiMethylethyl) 5-(PhenylMethyl) Ester

There total 4 articles about N,N-Bis[2-(1,1-diMethylethoxy)-2-oxoethyl]-L-glutaMic Acid 1-(1,1-DiMethylethyl) 5-(PhenylMethyl) 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%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-2-aminopentanedioic acid 5-benzyl ester 1-tert-butyl ester (80165-23-7,83718-99-4) → 2-bis(tert-butoxycarbonylmethyl)aminopentanedioic acid 5-benzyl ester 1-tert-butyl ester (862778-54-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/acs.biomac.7b00162

Reference yield: 89.0%

bromoacetic acid tert-butyl ester (5292-43-3) + L-glutamic acid γ-benzyl α-tert-butyl ester hydrochloride (105590-97-4) → 2-bis(tert-butoxycarbonylmethyl)aminopentanedioic acid 5-benzyl ester 1-tert-butyl ester (862778-54-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60 ℃; for 13h;

DOI:10.1021/ja907066r

Reference yield: 88.0%

4(S)-t-butoxycarbonyl-4-aminobutyric acid benzyl ester + bromoacetic acid tert-butyl ester (5292-43-3) → Bzl-Glu-NTA (862778-54-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 55 ℃;

upstream raw materials:

bromoacetic acid tert-butyl ester

(S)-2-aminopentanedioic acid 5-benzyl ester 1-tert-butyl ester

L-glutamic acid γ-benzyl α-tert-butyl ester hydrochloride

t-butoxycarbonyl-γ-aminobutyric acid

Downstream raw materials:

2-(bis-tert-butoxycarbonylmethylamino)-pentanedioic acid 1-tert-butyl ester

Glu-NTA

Refernces

• 1、 Liu, Juan,Spulber, Mariana,Wu, Dalin,Talom, Renee M.,Palivan, Cornelia G.,Meier, Wolfgang. "Poly(N -isopropylacrylamide- co -tris-nitrilotriacetic acid acrylamide) for a combined study of molecular recognition and spatial constraints in protein binding and interactions". . p. 12607 - 12614. Retrieved 2014.
• 2、 Gatterdam, Karl,Joest, Eike F.,Gatterdam, Volker,Tampé, Robert. "The Scaffold Design of Trivalent Chelator Heads Dictates Affinity and Stability for Labeling His-tagged Proteins in vitro and in Cells". supporting information. p. 12395 - 12399. Retrieved 2018/09/18.