CAS 3190-71-4

γ-Benzyl L-glutamate N-carboxyanhydride

Description:

γ-Benzyl L-glutamate N-carboxyanhydride (CAS 3190-71-4) is a cyclic imide derived from L-glutamic acid, characterized by its unique structure that includes a benzyl group attached to the gamma position of the glutamate side chain. This compound is a type of N-carboxyanhydride (NCA), which is known for its role in the synthesis of polypeptides and proteins through ring-opening polymerization. It is typically a white to off-white solid that is soluble in organic solvents such as dichloromethane and dimethylformamide. The presence of the benzyl group enhances its hydrophobic properties, making it useful in various applications, including drug delivery systems and biomaterials. Additionally, γ-Benzyl L-glutamate N-carboxyanhydride is sensitive to moisture and should be handled under an inert atmosphere to prevent hydrolysis. Its reactivity and ability to form stable polymers make it a valuable compound in synthetic organic chemistry and materials science.

Formula: C₁₃H₁₃NO₅

InChI: InChI=1S/C13H13NO5/c15-11(18-8-9-4-2-1-3-5-9)7-6-10-12(16)19-13(17)14-10/h1-5,10H,6-8H2,(H,14,17)

InChI key: InChIKey=UGCBVSDSTGUPBC-UHFFFAOYSA-N

SMILES: C(CC(OCC1=CC=CC=C1)=O)C2NC(=O)OC2=O

Synonyms:

• (+)-(S)-Glutamic acid γ-benzyl ester N-carboxyanhydride
• (S)-benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate
• 2,5-Dioxo-4-Oxazolidinepropanoic acidPhenylmethyl ester
• 4-Oxazolidinepropanoic acid, 2,5-dioxo-, phenylmethyl ester, (4S)-
• 4-Oxazolidinepropanoic acid, 2,5-dioxo-, phenylmethyl ester, (S)-
• 4-Oxazolidinepropionic acid, 2,5-dioxo-, benzyl ester, <span class="text-smallcaps">L</span>-
• 5-Benzyl <span class="text-smallcaps">L</span>-glutamate N-carboxyanhydride
• 5-Benzyl L-Glutamate N-Carboxyanhydride
• <span class="text-smallcaps">L</span>-Glutamic acid carboxyanhydride γ-benzyl ester
• <span class="text-smallcaps">L</span>-Glutamic acid-γ-benzyl ester N-carboxyanhydride
• <span class="text-smallcaps">L</span>-γ-Benzylglutamic acid carboxyanhydride
• Benzyl glutamate N-carboxyanhydride
• Glu(OBzl)-NCA
• H-Glu(Bzl)-NCA
• H-Glu(Obzl)-Nca
• N-Carboxy-γ-benzyl-<span class="text-smallcaps">L</span>-glutamate anhydride
• N-Carboxyanhydride γ-benzyl <span class="text-smallcaps">L</span>-glutamate
• benzyl 3-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]propanoate
• γ-Benzyl <span class="text-smallcaps">L</span>-N-carboxyglutamic anhydride
• γ-Benzyl <span class="text-smallcaps">L</span>-glutamate N-carboxyanhydride
• γ-Benzyl <span class="text-smallcaps">L</span>-glutamate-N-carboxylic anhydride
• γ-Benzyl N-carboxy-<span class="text-smallcaps">L</span>-glutamic anhydride
• γ-Benzyl glutamate N-carboxyanhydride
• γ-Benzyl glutamate NCA
• γ-Benzyl-<span class="text-smallcaps">L</span>-glutamic acid N-carboxyanhydride
• γ-Benzyl-<span class="text-smallcaps">L</span>-glutamic acid carboxyanhydride
• γ-Benzyl-N-carboxy-<span class="text-smallcaps">L</span>-glutamate anhydride
• 4-Oxazolidinepropionic acid, 2,5-dioxo-, benzyl ester, L-

H-GLU(OBZL)-NCA

CAS: 3190-71-4

Formula: C₁₃H₁₃NO₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 263.2460

Ref: IN-DA00C0SA

(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate

CAS: 3190-71-4

(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate

Purity: 99%

Molecular weight: 263.25g/mol

Ref: 54-OR80482

(4S)-2,5-Dioxo-4-oxazolidinepropanoic Acid Phenylmethyl Ester

Controlled Product

CAS: 3190-71-4

Stability Unstable in Solution
Applications (4S)-2,5-Dioxo-4-oxazolidinepropanoic Acid Phenylmethyl Ester was used in the synthesis and physicochemical characterization of reduction-sensitive block copolymer for intracellular delivery of doxorubicin.
References Jain, R., et al.: Langmuir, 28, 15323 (2012);

Formula: C₁₃H₁₃NO₅

Color and Shape: Neat

Molecular weight: 263.25

Ref: TR-D486830

5-Benzyl L-glutamate N-carboxyanhydride

CAS: 3190-71-4

5-Benzyl L-glutamate N-carboxyanhydride is a reactive derivative of L-glutamic acid, where the amino acid has been cyclised as an N-carboxyanhydride (NCA), a class of reagent known as Leuchs’ anhydrides. 5-Benzyl L-glutamate N-carboxyanhydride reacts with nucleophiles such as alcohols and amines to form esters and amides respectively. The opening of the N-carboxyanhydride to an ester or amide releases the amino acid amine which can also react as a nucleophile leading to polymerisation. These poly-amide polymers have been investigated as delivery platforms of Small Interfering RNA (si-RNA).

Formula: C₁₃H₁₃NO₅

Purity: Min. 95 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 263.25 g/mol

Ref: 3D-FB63140

ε-Benzyl-L-glutamic acid carboxylic anhydride

CAS: 3190-71-4

Formula: C₁₃H₁₃NO₅

Purity: 95%

Color and Shape: Solid

Molecular weight: 263.249

Ref: 10-F044842