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Introduction of N-Cbz-L-Glutamic Acid 5-tert-Butyl Ester is a protected derivative of L-glutamic acid, used in peptide synthesis. It features two protecting groups:
N-Cbz (Carboxybenzyl) on the amino group (removable by hydrogenolysis).
tert-Butyl ester on the γ-carboxylic acid (cleavable with acid).
This dual protection allows selective reactions at the α-carboxylic acid during peptide chain assembly while preventing unwanted side reactions. It retains the natural L-configuration and is soluble in organic solvents. Commonly employed in drug discovery and solid-phase peptide synthesis, it ensures controlled deprotection steps. Handle with care (moisture/light-sensitive) and store under inert conditions.
Description of N-Cbz-L-Glutamic acid 5-tert-butyl ester from Wuhan Fortuna Chemical Co.,Ltd
Basic Information of N-Cbz-L-Glutamic acid 5-tert-butyl ester | |
Product Name | |
CAS NO. | |
Apperance | White Powder |
Assay | 99.9% |
Pacakge | 1kg/Foil Bag, 25kg/ Box/carton |
MOQ | 1kg |
Storage | |
Shelf Life | 2 Years |
Brand | Fortunachem |
Specifications(COA) of N-Cbz-L-Glutamic acid 5-tert-butyl ester CAS 3886-08-6
Items | Specifications | Results |
Appearance | White Powder | White Powder |
Solubility | 0.5mmole in 1ml DMF clearly soluble | Clearly soluble |
IR Spectrum | In accordance with structure | In accordance with structure |
Melting point | 83.0-91.0℃ | 85.8-86.2℃ |
Specific Rotation | -14.0±1.0°(C=2,Methanol) | -14.3°(C=2,Methanol) |
Optical Purity(HPLC) | ≤0.30%D-enantiomer | Not detected |
Water(K.F) | ≤1.0% | 0.1% |
Z-Glu-OH(HPLC) | 0.006% | |
Free Glu TLC Analysis | ＜0.05% | |
Any other impurity | ≤0.30% | 0.03% |
Purity(HPLC) | ≥99.0%(Area%) | 99.9% |
Assay(AT) | ≥98.0%(AT) | 99.6% |
Acetic acid ions(IC) | ≤100mg/kg | 34.32mg/kg |
Residual Solvent | ≤0.50%petroleum ether | 0.080% 0.042% |
Conclusion | Meets our standard | |
Introduction of N-Cbz-L-Glutamic Acid 5-tert-Butyl Ester is a protected derivative of L-glutamic acid, used in peptide synthesis. It features two protecting groups:
N-Cbz (Carboxybenzyl) on the amino group (removable by hydrogenolysis).
tert-Butyl ester on the γ-carboxylic acid (cleavable with acid).
This dual protection allows selective reactions at the α-carboxylic acid during peptide chain assembly while preventing unwanted side reactions. It retains the natural L-configuration and is soluble in organic solvents. Commonly employed in drug discovery and solid-phase peptide synthesis, it ensures controlled deprotection steps. Handle with care (moisture/light-sensitive) and store under inert conditions.
Application of N-Cbz-L-Glutamic Acid 5-tert-Butyl Ester is a chemically modified derivative of the amino acid L-glutamic acid, designed for use in organic synthesis, particularly in peptide chemistry. Below is a detailed breakdown:
1. Core Structure: Based on L-glutamic acid, which has:
An α-amino group (NH₂) at position 1.
Two carboxylic acid groups:
α-carboxylic acid (adjacent to the amino group).
γ-carboxylic acid (on the side chain, at position 5).
A three-carbon side chain.
2. Protecting Groups:
N-Cbz (Carboxybenzyl):
Protects the α-amino group (NH₂) as a benzyloxycarbonyl (Cbz) group.
Provides stability during synthesis and is removable via hydrogenolysis (e.g., using H₂/Pd).
5-tert-Butyl Ester:
Protects the γ-carboxylic acid (position 5) as a tert-butyl ester.
Stable under basic conditions but cleavable under acidic conditions (e.g., trifluoroacetic acid, TFA).
Peptide Synthesis:
Serves as a building block to incorporate glutamic acid into peptides while preventing unwanted side reactions at the amino and γ-carboxylic acid groups.
Enables selective deprotection and activation of the α-carboxylic acid for forming peptide bonds.
Medicinal Chemistry: Used in drug discovery to synthesize glutamic acid-containing compounds with controlled reactivity.
Physical Form: Typically a white to off-white crystalline powder.
Solubility: Soluble in organic solvents (e.g., DMF, DCM) but poorly soluble in water due to the tert-butyl ester.
Stereochemistry: Retains the natural L-configuration of glutamic acid, critical for biological activity.
Orthogonal Protection:
Allows sequential deprotection (e.g., remove Cbz first via hydrogenolysis, then tert-butyl ester via acid).
Facilitates complex multi-step syntheses in peptide chains or functionalized molecules.
Stability: Sensitive to light, moisture, and strong acids/bases.
Hazards:
Use gloves/eye protection to avoid irritation.
Avoid inhaling dust; handle in a fume hood.
Storage: Keep in a cool, dry place under inert atmosphere (e.g., N₂).
Z-L-Glutamic Acid 5-OtBu Ester ("Z" = Cbz group).
CAS Number: 1676-73-9.
In synthesizing a peptide containing glutamic acid:
1. Use N-Cbz-L-Glutamic acid 5-tert-butyl ester to couple the α-carboxylic acid to another amino acid.
2. Remove the Cbz group with H₂/Pd to expose the amino group for further coupling.
3. Cleave the tert-butyl ester with TFA to free the γ-carboxylic acid in the final deprotection step.
This compound is essential for precision in synthetic organic chemistry, enabling controlled construction of bioactive molecules.
FAQ From Wuhan Fortuna Chemical Co.,Ltd | |
Q | Can I get a sample for free ? |
A | For small QTY and low value product, we can provide sample for free exclude shipping cost. For high value sample, we will charge the basic sample cost, but we can refund all the cost if customers place order after sample test. |
Q | How to confirm the product quality before placing orders ? |
A | Most of our products confirm to international standards like USP/EP/BP/JP/CP. We will provide COA/TDS/MSDS for customers to confirm the specification before placing order. |
Q | What is the payment you accept? |
A | For small and low value order, we accept CreditCard, MaterCard,VISA,Western Union and T/T.For large order, we can do T/T and L/C. Any pay on delivery or pay-after are not available for us. |
Q | What is your shipment way ? |
A | For less than 100kg gross weight order will ship with courier like FedEx or UPS, we support customers to place courier orders remotely by their account, we will package the goods well and wait for pick up.For more than 100kg goods, we will transport by Air or Sea according to customers' requirement. |
Q | How long is your after-sales service? |
A | We accept customer’s quality complaint in three month after customer received the goods. We provide tech.support for all-life if customer place order from our company. |
How do you treat quality complaint ? | |
A | We support customer to provide our products to any rightful third party testing organization to test our products according to the COA specification, if the test result is confirm with COA, we will take all the loss for customers. |
Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical and Intermediates, Food and Feed additives, Fine chemicals,Biochemical and Reagent, which is the members of Hubei E-commerce Chamber.
Our company has professional persons who major in chemical R&D and sicentific management, supply fine chemical products with high quality and close service, also supply custom-tailored products according to our clients' requirement.
We have a positive and self-motivated management work team with a common philosophy, caring and commitment through teamwork, our team strive to achieve success in delighting our clients and ourselves.
Since Wuhan Fortuna Chemical Co., Ltd founded, we continuously innovate our products and improve our service, sales network. Hence, we initiate the first sale mode on net in China, which is the retail trade of small package bring along wholesale of diversified management modes. Our products are exported widely to South Korea, Vietnam, Australia, Europe and South America, highly recommended by our clients.We insist on the management creed “Market is our compass, Quality is our life, Credit is our soul”. Clients’ trust is our forward power, their satisfaction is our struggling goal.
Wuhan Fortuna Chemical Co.,Ltd is a professional manufacturer which provide N-Cbz-L-Glutamic acid 5-tert-butyl ester with good quality and best price, welcome to contact us to get COA/TDS/MSDS of N-Cbz-L-Glutamic acid 5-tert-butyl ester.
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