19794-10-6

Basic information

• Product Name: BOC-ALA-ALA-OME
• Synonyms: BOC-L-ALANYL-L-ALANINE METHYL ESTER;BOC-ALA-ALA-OME;(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)propanoate;REF DUPL: Boc-Ala-Ala-OMe;N-[(tert-Butoxy)carbonyl]-L-alanyl-L-alanine methyl ester;N-[N-[(tert-Butoxy)carbonyl]-L-alanyl]-L-alanine methyl ester;N-Boc-L-alanyl-L-alanine Methyl ester, 97%;Boc-L-Ala-L-Ala-OMe
• CAS NO: 19794-10-6
• Molecular Formula: C₁₂H₂₂N₂O₅
• Molecular Weight: 274.31
• Mol File: 19794-10-6.mol
• Article Data: 50

Chemical Properties

• Melting Point: 110-111℃
• Appearance: /
• Density: 1.101
• CAS DataBase Reference: BOC-ALA-ALA-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ALA-ALA-OME(19794-10-6)
• EPA Substance Registry System: BOC-ALA-ALA-OME(19794-10-6)

Safety Data

• Hazardous Substances Data: 19794-10-6(Hazardous Substances Data)

Usage

General Description

BOC-ALA-ALA-OME is a chemical compound that consists of two molecules of aminolevulinic acid (ALA) linked together through a bond to a tert-butyloxycarbonyl (BOC) protecting group, and an omega-methyl ester group at one end. Aminolevulinic acid is a naturally occurring compound in the body that plays a role in the synthesis of heme, an important component of hemoglobin and other iron-containing proteins. BOC-ALA-ALA-OME is often used as a building block in the synthesis of peptide and protein-based drugs, as well as in research and development of new pharmaceuticals. The BOC protecting group allows for specific reactions to occur at the amino acid group, while the omega-methyl ester group can be selectively removed or manipulated to alter the compound's properties.

Upstream product

• 15761-38-3 L-N-Boc-Ala 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 50903-48-5 N-tert.butyloxycarbonyl-alanine pentafluorophenyl ester 
• 128369-70-0 (S)-methyl 2-(((allyloxy)carbonyl)amino)propanoate 
• 10065-72-2 L-Alanine methyl ester 
• 3392-10-7 tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester 
• 13515-97-4 methyl 2-aminopropanoate monohydrochloride 
• 1146929-22-7 (S)-O-(tert-butyl) N-(thietan-2-on-3-yl) carbamate 
• 133039-96-0 (S)-(1-fluoro-1-oxoprop-2-yl)carbamic acid tert-butyl ester 
• 3744-87-4 Boc-(R)-Ala 
• 14316-06-4 D-alanine methyl ester hydrochloride 
• 1280225-71-9 C₁₈H₂₈N₂O₆ 
• 170454-73-6 (S)-2-((R)-2-tert-Butoxycarbonylamino-3-iodo-propionylamino)-propionic acid methyl ester 
• 66024-53-1 BOC-Ala-POBT 

Downstream Products

• 27317-69-7 N-tert-butoxycarbonyl-L-alanyl-L-alanine 
• 73998-02-4 N-(tert-butoxycarbonyl)-L-alanyl-D-alanine 
• 41036-19-5 L-alanyl-alanine methylester hydrochloride 
• 70396-27-9 Boc-L-phenylalanyl-L-alanyl-L-alanine methyl ester 
• 41036-27-5 H-Ala₃-OMe*HCl 
• 155518-27-7 N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester 
• 160480-13-7 Boc-Tyr-Ala-Ala-OH 
• 1429338-47-5 Boc-Tyr-Ala-Ala-OMe 
• 1620161-80-9 (S)-perfluorophenyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 
• 1422736-96-6 Bz-VGAψ[CSe-NH]AA-NH2 

Relevant articles and documents

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Restrictions on the binding of proline-containing peptides to elastase.

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Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives

Marine natural products derived from special or extreme environment provide an important source for the development of anti-tumor drugs due to their special skeletons and functional groups. In this study, based on our previous work on the total synthesis and structure revision of the novel marine natural product Chrysamide B, a group of its derivatives were designed, synthesized, and subsequently of which the anti-cancer activity, structure-activity relationships and cellular mechanism were explored for the first time. Compared with Chrysamide B, better anti-cancer performance of some derivatives against five human cancer cell lines (SGC-7901, MGC-803, HepG2, HCT-116, MCF-7) was observed, especially for compound b-9 on MGC-803 and SGC-7901 cells with the IC 50 values of 7.88 ± 0.81 and 10.08 ± 1.08 μM, respectively. Subsequently, cellular mechanism study suggested that compound b-9 treatment could inhibit the cellular proliferation, reduce the migration and invasion ability of cells, and induce mitochondrial-dependent apoptosis in gastric cancer MGC-803 and SGC-7901 cells. Furthermore, the mitochondrial-dependent apoptosis induced by compound b-9 is related with the JAK2/STAT3/Bcl-2 signaling pathway. To conclude, our results offer a new structure for the discovery of anti-tumor lead compounds from marine natural products.