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BOC-ALA-ALA-OME is a chemical compound composed of two molecules of aminolevulinic acid (ALA) connected through a bond to a tert-butyloxycarbonyl (BOC) protecting group, with an omega-methyl ester group at one end. Aminolevulinic acid is a naturally occurring compound involved in the synthesis of heme, a vital component of hemoglobin and other iron-containing proteins. BOC-ALA-ALA-OME serves as a building block in the synthesis of peptide and protein-based drugs and is utilized in research and development for new pharmaceuticals. The BOC protecting group facilitates specific reactions at the amino acid group, while the omega-methyl ester group can be selectively removed or modified to change the compound's properties.

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  • 19794-10-6 Structure
  • Basic information

    1. Product Name: BOC-ALA-ALA-OME
    2. 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
    3. CAS NO:19794-10-6
    4. Molecular Formula: C12H22N2O5
    5. Molecular Weight: 274.31
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 19794-10-6.mol
  • Chemical Properties

    1. Melting Point: 110-111℃
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.101
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: BOC-ALA-ALA-OME(CAS DataBase Reference)
    10. NIST Chemistry Reference: BOC-ALA-ALA-OME(19794-10-6)
    11. EPA Substance Registry System: BOC-ALA-ALA-OME(19794-10-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 19794-10-6(Hazardous Substances Data)

19794-10-6 Usage

Uses

Used in Pharmaceutical Synthesis:
BOC-ALA-ALA-OME is used as a building block for the synthesis of peptide and protein-based drugs, contributing to the development of novel pharmaceuticals with potential therapeutic applications.
Used in Research and Development:
In the pharmaceutical industry, BOC-ALA-ALA-OME is utilized in research and development to explore its potential in creating new drugs and understanding its chemical properties and interactions.
Used in Chemical Reactions:
The BOC protecting group in BOC-ALA-ALA-OME allows for specific reactions to occur at the amino acid group, which is crucial for the synthesis of complex molecules and the development of advanced drug candidates.
Used in Property Manipulation:
The omega-methyl ester group in BOC-ALA-ALA-OME can be selectively removed or manipulated, enabling the alteration of the compound's properties to suit specific pharmaceutical applications or to enhance its effectiveness in drug delivery systems.

Check Digit Verification of cas no

The CAS Registry Mumber 19794-10-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,9 and 4 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 19794-10:
(7*1)+(6*9)+(5*7)+(4*9)+(3*4)+(2*1)+(1*0)=146
146 % 10 = 6
So 19794-10-6 is a valid CAS Registry Number.

19794-10-6Relevant articles and documents

Bicomponent β-sheet assembly of dipeptide fluorophores of opposite polarity and sensitive detection of nitro-explosives

Madhu, Chilakapati,Roy, Bappaditya,Makam, Pandeeswar,Govindaraju, Thimmaiah

, p. 2280 - 2283 (2018)

Fluorescent hydrogels of two dipeptide-pyrene amphiphiles of opposite polarity are developed via bicomponent antiparallel β-sheet co-assembly. The helical molecular assembly resulted in the formation of fluorescent nanofibers. The sandwich-like interaction of nitroaromatics within the hydrogel matrix enabled selective and sensitive detection of toxic nitro-explosives.

Backbone thioamide directed macrocyclisation: Lactam stapling of peptides

Hutton, Craig A.,Taresh, Ameer B.

supporting information, p. 1488 - 1492 (2022/03/01)

A novel method for lactam stapling of Asp/Lys-containing peptides has been developed that does not require coupling agents. A backbone thioamide is incorporated at the N-terminal side of the aspartate residue. Ag(i)-promoted activation of the thioamide in the vicinity of the Asp carboxylate generates a cyclic isoimide intermediate that is trapped by the Lys amine to generate the macrolactam. This method is suitable for generation of i,i+2, i,i+3, and i,i+4-spaced lactam-bridged peptides. This journal is

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

Brittain, William D. G.,Cobb, Steven L.

supporting information, p. 5793 - 5798 (2021/08/01)

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%.

Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation

Zhu, Long-Qing,Fan, Xiao-Hong,Li, Jun-Fang,Chen, Jin-Hong,Liang, Yan,Hu, Xiao-Ling,Ma, Shu-Meng,Hao, Xiang-Yong,Shi, Tao,Wang, Zhen

supporting information, (2021/05/26)

Inflammation as a host's excessive immune response to stimulation, is involved in the development of numerous diseases. To discover novel anti-inflammatory agents and based on our previous synthetic work on marine natural product Chrysamide B, it and a series of derivatives were synthesized and evaluated for their anti-inflammatory activity on inhibition of LPS-induced NO production. Then the preliminary structure–activity relationships were conducted. Among them, Chrysamide B is the most potent anti-inflammatory agent with low cytotoxicity and strong inhibition on the production of NO (IC50 = 0.010 μM) and the activity of iNOS (IC50 = 0.082 μM) in LPS-stimulated RAW 264.7 cells. Primary studies suggested that the mechanism of action may be that it interfered the formation of active dimeric iNOS but not affected transcription and translation. Furthermore, its good performance of anti-inflammatory effect on LPS-induced multiple inflammatory cytokines production, carrageenan-induced paw edema, and endotoxin-induced septic mice, was observed. We believe that these findings would provide an idea for the further modification and research of these analogs in the future.

Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives

Zhu, Longqing,Li, Junfang,Fan, Xiaohong,Hu, Xiaoling,Chen, Jinhong,Liu, Yonghong,Hao, Xiangyong,Shi, Tao,Wang, Zhen,Zhao, Quanyi

, (2021/04/29)

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.

ANTI-HUMAN VISTA ANTIBODIES AND USE THEREOF

-

Paragraph 442; 564, (2021/10/30)

The invention provides anti-VISTA antibody drug conjugates which may be used for targeted delivery of anti-inflammatory agents such as steroids to immune cells, e.g., myeloid cells. The invention also provides methods of using anti-VISTA antibody drug conjugates in the treatment of inflammatory and/or autoimmune conditions and/or for alleviating the toxicity of anti-inflammatory agents such as steroids.

Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies

Qin, Minggao,Zhang, Yaqian,Xing, Chao,Yang, Li,Zhao, Changli,Dou, Xiaoqiu,Feng, Chuanliang

, p. 3119 - 3129 (2021/01/20)

Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series o

Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers

Freire, Félix,Qui?oá, Emilio,Riguera, Ricardo,Suárez-Picado, Esteban

supporting information, p. 4537 - 4543 (2020/02/04)

The dynamic behavior of helical polymers bearing pendant groups with two chiral centers was studied. Controlled conformational changes at the chiral units placed either closer to or further away from the main chain promote different helical structures. Al

Phosphonopeptides revisited, in an era of increasing antimicrobial resistance

Anderson, Rosaleen J.,Bedernjak, Alexandre F.,Cummings, Stephen P.,Day, Kathryn M.,Gray, Mark,Jones, Amanda L.,Marrs, Emma C. L.,Perry, John D.,Varadi, Linda

supporting information, (2020/03/26)

Given the increase in resistance to antibacterial agents, there is an urgent need for the development of new agents with novel modes of action. As an interim solution, it is also prudent to reinvestigate old or abandoned antibacterial compounds to assess

Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

Wróbel, Agnieszka,Kolesińska, Beata,Fr?czyk, Justyna,Kamiński, Zbigniew J.,Tankiewicz-Kwedlo, Anna,Hermanowicz, Justyna,Czarnomysy, Robert,Maliszewski, Dawid,Drozdowska, Danuta

, p. 990 - 1002 (2019/11/03)

This study provides new information on the cellular effects of 1,3,5-triazine nitrogen mustards with different peptide groups in DLD and Ht-29 human colon cancer cell lines. A novel series of 2,4,6-trisubstituted 1,3,5-triazine derivatives bearing 2-chloroethyl and oligopeptide moieties was designed and synthesized. The most cytotoxic derivative was triazine with an Ala-Ala-OMe substituent on the ring (compound 7b). This compound induced time- and dose-dependent cytotoxicity in the DLD-1 and HT-29 colon cancer cell lines. The triazine derivative furthermore induced apoptosis through intracellular signaling pathway attenuation. Compound 7b may be a candidate for further evaluation as a chemotherapeutic agent against colorectal cancer.

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