604003-91-0

Basic information

• Product Name: H2N-L-PRO-OME
• Synonyms: N-ALPHA-AMINO-L-PROLINE METHYL ESTER;H2N-L-PRO-OME;L-Proline, 1-amino-, methyl ester (9CI)
• CAS NO: 604003-91-0
• Molecular Formula: C6H12N2O2
• Molecular Weight: 144.17
• Product Categories: CARBOXYLICESTER
• Mol File: 604003-91-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: H2N-L-PRO-OME(CAS DataBase Reference)
• NIST Chemistry Reference: H2N-L-PRO-OME(604003-91-0)
• EPA Substance Registry System: H2N-L-PRO-OME(604003-91-0)

Safety Data

• Hazardous Substances Data: 604003-91-0(Hazardous Substances Data)

Usage

General Description

H2N-L-PRO-OME is a chemical compound consisting of the amino acid proline (PRO) with a methyl ester group (OME) attached to its carboxyl end. H2N-L-PRO-OME is commonly used in peptide synthesis and research, as the methyl ester group can help protect the carboxyl group during the synthesis process. Proline is a non-essential amino acid that plays a crucial role in protein structure and function, particularly in collagen and elastin formation. By incorporating H2N-L-PRO-OME into peptides, researchers can study the effects of proline on protein folding, stability, and interactions within biological systems.

Upstream product

• 77821-22-8 (S)-1-tert-butoxycarbonylaminopyrrolidine-2-carboxylic acid 
• 71922-04-8 (S)-1-nitrosopyrrolidine-2-carboxylic acid methyl ester 
• 7519-36-0 nitrosoproline 
• 147-85-3 L-proline 

Relevant articles and documents

Prolinimines: N-Amino- l -Pro-methyl Ester (Hydrazine) Schiff Bases from a Fish Gastrointestinal Tract-Derived Fungus, Trichoderma sp. CMB-F563

A rice cultivation of a fish gastrointestinal tract-derived fungus, Trichoderma sp. CMB-F563, yielded natural products incorporating a rare hydrazine moiety, embedded within a Schiff base. Structures inclusive of absolute configurations were assigned to prolinimines A-D (1-4) on the basis of detailed spectroscopic and C3 Marfey's analysis, as well as biosynthetic considerations, biomimetic total synthesis, and chemical transformations. Of note, monomeric 1 proved to be acid labile and, during isolation, underwent quantitative transformation to dimeric 3 and trimeric 4. Prolinimines are only the second reported natural products incorporating an N-amino-Pro residue, the first to include l-Pro, the first to occur as Schiff bases, and the first to be isolated from a microorganism.

N- and C-terminal modifications of negamycin

Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected β-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50=2.3 μM), has antibacterial activity (Escherichia coli, MIC=16 μg/mL), and is efficacious in an E. coli murine septicemia model (ED50=16.3 mg/kg).