51803-69-1

Basic information

• Product Name: BOC-VAL-GLY-OME
• Synonyms: BOC-VAL-GLY-OME;Glycine, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-, methyl ester;methyl (tert-butoxycarbonyl)-L-valylglycinate
• CAS NO: 51803-69-1
• Molecular Formula: C₁₃H₂₄N₂O₅
• Molecular Weight: 288.34
• Mol File: 51803-69-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-VAL-GLY-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-VAL-GLY-OME(51803-69-1)
• EPA Substance Registry System: BOC-VAL-GLY-OME(51803-69-1)

Safety Data

• Hazardous Substances Data: 51803-69-1(Hazardous Substances Data)

Upstream product

• 13734-41-3 t-Boc-L-valine 
• 616-34-2 methoxycarbonylmethylamine 
• 133010-02-3 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-methylpropyl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72-18-4 L-valine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 66866-46-4 C₁₅H₂₇NO₆ 
• 126748-96-7 C₁₈H₃₄N₃O₇P 

Downstream Products

• 45233-75-8 2-[[(2S)-2-(tert-butoxycarbonylamino)-3-methyl-butanoyl]amino]acetic acid 
• 20902-47-0 N-tert-butoxycarbonyl-L-valyl-L-phenylalanine methyl ester 
• 957753-07-0 (R)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-phenylpropanoate 
• 17498-50-9 L-valine hydrochloride 

Relevant articles and documents

Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives

Modification of amino acids is an important strategy in organic and bioorganic chemistry. In contrast to common side-chain functionalization, backbone modification is much less explored. Especially glycine units seem to be attractive and versatile since a wide range of functionality can be potentially introduced. We report here oxidative modification of glycinates that are stable and enable further functionalization. Selective glycinate enolate oxidation by TEMPO or a FeCp2PF6/TEMPO reagent combination provides stable alkoxyamines in good to excellent yields. The methodology is expanded to glycine-containing dipeptides demonstrating selective oxygenation at the glycine unit. The orthogonal reactivity potential of oxygenated glycines for transformation to other amino acid derivatives is explored.

Optimization and anti-cancer properties of fluoromethylketones as covalent inhibitors for ubiquitin C-terminal hydrolase L1

The deubiquitinating enzyme (DUB) UCHL1 is implicated in various disease states including neurodegenerative disease and cancer. However, there is a lack of quality probe molecules to gain a better understanding on UCHL1 biology. To this end a study was carried out to fully characterize and optimize the irreversible covalent UCHL1 inhibitor VAEFMK. Structure-activity relationship studies identified modifications to improve activity versus the target and a full cellular characterization was carried out for the first time with this scaffold. The studies produced a new inhibitor, 34, with an IC50 value of 7.7 μM against UCHL1 and no observable activity versus the closest related DUB UCHL3. The molecule was also capable of selectively inhibiting UCHL1 in cells and did not demonstrate any discernible off-target toxicity. Finally, the molecule was used for initial probe studies to assess the role of UCHL1 role in proliferation of myeloma cells and migration behavior in small cell lung cancer cells making 34 a new tool to be used in the biological evaluation of UCHL1.

Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs

Curcumin (CUR) is a natural yellow pigment from turmeric with extensive bioactivities. However its relatively poor solubility limited its absorption and bioavailability. In this study, a novel series of CUR-peptide conjugates were designed and synthesized

Preparation of Constrained Unnatural Aromatic Amino Acids via Unsaturated Diketopiperazine Intermediate

Unnatural aromatic amino acids are useful tools in drug discovery, since their insertion in bioactive peptide sequences can change the side chains spatial orientation, the backbone conformation and above all, their bioactivity. In this communication, we propose a straightforward method to synthesize 2′,6′-dimethyl-tyrosine and 2′,6′-dimehylphenyl-alanine derivatives as handling building blocks for peptide synthesis via unsaturated diketopiperazine (DKP) intermediate.

AGRICULTURAL PLANT-PROTECTING AGENTS CONTAINING DIPEPTIDE DERIVATIVE AS ACTIVE INGREDIENT

Provided is an agricultural plant-protecting agent including a dipeptide derivative or an agro-pharmaceutically acceptable salt thereof as an active ingredient, which has a plant disease-preventing effect, a plant growth-promoting effect, and a plant immunity-activating effect.

Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors

A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds against SKOV3, HL60 and A549 cells were also investigated. Comparing with the control LY52, compound 12u, with excellent activity both in the enzymatic inhibition assay and cell-based assay, could be used as lead compound for the further development of MMP inhibitors.

A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines

Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the product diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds.

COMPOUNDS FOR AMIDE-FORMING REACTIONS

Provided herein is a compound of Formula I, that displays remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water, wherein said coupling reactions proceed without measurable racemization. A method of pro

A new oxyma derivative for nonracemizable amide-forming reactions in water

An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could b

Bioinspired modular synthesis of elastin-mimic polymers to probe the mechanism of elastin elasticity

Bioinspired modular synthesis of elastin-mimic polymers (EMPs) is achieved via Cu-catalyzed alkyne-azide cyclization (CuAAC). By changing the module, EMPs with different secondary structures determined by circular dichroism (CD) spectra in trifluoroethanol (TFE) solution are obtained. The EMPs are characterized by measuring the lower critical solution temperatures (LSCTs) and the bulk mechanic properties under the conditions of both dry and hydrated forms. The unique molecular design enables us to probe mechanistic questions and assess the structure-property relationship of the EMPs. Our results indicate that, instead of a highly organized secondary structure, hydrophobic hydration is critical for the elasticity of EMPs.