686-50-0

Basic information

• Product Name: H-LEU-GLY-OH
• Synonyms: Leu-Gly-OH≥ 95% (HPLC);L-LEUCYL-GLYCINE;L-LEU-GLY;LEU-GLY;H-LEU-GLY-OH;Leu-Gly hydrate;N-L-leucylglycine;leu-glycrystalline
• CAS NO: 686-50-0
• Molecular Formula: C₈H₁₆N₂O₃
• Molecular Weight: 188.22
• EINECS: 211-688-9
• Product Categories: Biochemistry;Oligopeptides;Peptide Synthesis;Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 686-50-0.mol

Chemical Properties

• Melting Point: ~245 °C (dec.)
• Boiling Point: 323.23°C (rough estimate)
• Appearance: /
• Density: 1.1793 (rough estimate)
• Refractive Index: 86 ° (C=2, H2O)
• Storage Temp.: −20°C
• PKA: 3.25(at 25℃)
• CAS DataBase Reference: H-LEU-GLY-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-LEU-GLY-OH(686-50-0)
• EPA Substance Registry System: H-LEU-GLY-OH(686-50-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 686-50-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
H-LEU-GLY-OH is used as an inhibitor for ubiquitin-mediated proteolysis, a process that is essential for the regulation of various cellular functions, including protein homeostasis and signal transduction. By inhibiting this process, H-LEU-GLY-OH can potentially be utilized in the development of therapeutic strategies for diseases associated with abnormal protein degradation.
Used in Research and Development:
In the field of research and development, H-LEU-GLY-OH serves as a valuable compound for studying the mechanisms of protein degradation and the role of ubiquitin in cellular processes. This dipeptide can be used to develop new drugs or therapies targeting specific pathways involved in protein homeostasis and signal transduction.
Used in Drug Delivery Systems:
Similar to gallotannin, H-LEU-GLY-OH can also be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. By employing various organic and metallic nanoparticles as carriers, the delivery, efficacy, and targeting of H-LEU-GLY-OH can be improved, making it a more effective compound for treating specific conditions.

InChI:InChI=1/C8H16N2O3/c1-5(2)3-6(9)8(13)10-4-7(11)12/h5-6H,3-4,9H2,1-2H3,(H,10,13)(H,11,12)/t6-/m0/s1

Upstream product

• 7154-27-0 (+/-)-N-(2-bromo-4-methyl-valeryl)-glycine 
• 27560-15-2 methyl 2-(2-amino-4-methylpentanamido)acetate 
• 2706-38-9 N-(N-benzyloxycarbonyl-L-leucyl)-glycine 
• 47094-27-9 H-Leu-Gly-OBzl 
• 1187-50-4 L-Leu-Gly-Gly 
• 72-18-4 L-valine 
• 3190-70-3 L-Leucin-N-carbonsaeureanhydrid 
• 26117-20-4 N-carbamoyl-L-leucine 
• 6000-44-8 sodium glycinate 
• 2018-66-8 Z-Leu-OH 
• 2867-06-3 Benzyloxycarbonylleucyl-glycine ethyl ester 
• 111411-33-7 N-benzyloxycarbonyl-L-thioleucine S-(4-nitro-phenyl ester) 
• 28659-88-3 (R)-2-Bromo-4-methyl-pentanoyl chloride 
• 51220-76-9 (N-(tert-butoxycarbonyl)-L-leucinyl)glycine ethyl ester 

Downstream Products

• 92325-87-6 N-[N-(2,4-dinitro-phenyl)-L-leucyl]-glycine 
• 2706-38-9 N-(N-benzyloxycarbonyl-L-leucyl)-glycine 
• 53375-57-8 H-Leu-Gly-OEt 
• 135875-27-3 Z-Glu-Leu-Gly 
• 95753-58-5 N-Fmoc-L-Phe-(p-thiocarbamoyl-L-Leu-Gly)OMe 
• 95753-59-6 DL-5-(2-methylpropyl)-3-<4-<(2S)-Fmocamino-2-methoxycarbonylethyl>phenyl>-2-thiohydantoin 
• 82007-05-4 (Fmoc)-Leu-Gly-OH 
• 1385775-67-6 N-Cbz-L-Cys-L-Leu-Gly-OH 
• 1447757-94-9 C₂₆H₃₂N₄O₈ 
• 1447757-99-4 C₃₇H₄₃N₅O₁₁ 
• 63097-15-4 Z-Ala-Leu-Gly 

Relevant articles and documents

Stereoselective ring contraction of 2,5-diketopiperazines: An innovative approach to the synthesis of promising bioactive 5-membered scaffolds

Ring contraction of 2,5-diketopiperazines by TRAL-alkylation led us to the stereoselective synthesis of original pyrrolidine-2,4-diones, a novel series of promising molecules with moderate anti-proliferative activity on breast cancer cells.

DPP4 INHIBITOR AND PHARMACEUTICAL APPLICATION THEREOF

The present invention provides a Dpp4 inhibitor which comprises a leucine derivative of the following formula (1) or a methionine derivative of the following formula (2): wherein each R1 and R3 represents a hydrogen atom (H) and an L-amino acid residue; R2 represents a hydroxyl group (OH), alkoxy group having 1 to 6 carbon atoms, amino group (NH2), alkylamino group having 1 to 6 carbon atoms, glycine residue, β-alanine residue, L-amino acid (except for proline, alanine and phenylalanine) residue or L-amino-acid amide (except for proline amide, alanine amide and phenylalanine amide) residue; and R4 represents a hydroxyl group (OH), alkoxy group having 1 to 6 carbon atoms, amino group (NH2), alkylamino group having 1 to 6 carbon atoms, glycine residue, β-alanine residue, L-amino acid (except for proline and alanine) residue or L-amino-acid amide (except for proline amide and alanine amide) residue. These derivatives also act as autophagy regulators.

N-carbamoyl derivatives and their nitrosation by gaseous NOx - A new, promising tool in stepwise peptide synthesis

New uses of the N-carbamoyl group in peptide synthesis as an Nα-protecting group in classical peptide coupling methods, and as a preactivating group for stepwise coupling by NCA formation - are presented. In the first application, the N-carbamoyldipeptide esters C-Val-Gly-OEt, C-Leu-Gly-OEt, C-Ala-Gly-OEt, and C-Ala-Phe-OEt were obtained in good yields by treatment of the corresponding N-carbamoylamino acids (CAA) with amino acid esters. Quantitative N-deprotection without racemisation was then achieved in the solid through nitrosation by gaseous NOx. The extent of racemisation occurring in the coupling step is discussed. In the second application, an easy route to amino acid N-carboxy anhydrides (NCAs) through nitrosation of CAA under the same conditions as above allowed straightforward "one-pot" peptide stepwise coupling, as demonstrated by the formation of Leu-Gly and Val-Gly in good yields and enantiomeric excess. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Potential D,L-amino acid sequence analysis of peptides from the C-terminus

A model tripeptide, Gly-L-Leu-L-Phe, was immobilized with activated aminomethyl polystyrene, and its C-terminal was reduced to an alcohol. This peptidyl alcohol was selectively hydrolyzed at the C-terminal amide bond to afford a polymer-supported dipeptide (Gly-L-Leu) and amino alcohol (Phe-OH). The amino alcohol, including its absolute configuration, was determined by labelling with (+)-MNB-COOH, and the dipeptide was reused for a determination of its C-terminal amino acids. The D,L-amino acids of the tripeptide were sequentially determined from the C-terminus.

The Steric Hindrance of the Stepwise Reaction of N-Carboxy α-Amino Acid Anhydride with the α-Amino Acid Ester

The mechanisms of the reactions of 4-alkyloxazolidinediones (1) (N-carboxy α-amino acid anhydrides(NCAs)) with α-amino acid benzyl ester p-toluenesulfonates (2) were investigated in acetonitrile containing triethylamine at low and room temperatures.Two types of reactions were observed: (1) the polymerization of NCAs was initiated with a small amount of 2 to produce polypeptides (6), and (2) the dipeptide benzyl esters (4) were produced by the stepwise reaction of NCAs with the esters.Both the polymerization and the dipeptide formation (1+2) seemed to be initiated by the nucleophilic attack of the amino group of the ester on the C-5 carbon of NCAs.The polymerization proceeded when the side chains of the amino acid esters (R2) were more bulky than those of the NCAs (R1).On the contrary, dipeptide esters were produced when the side chains of the NCAs (R1) were more bulky than those of the esters (R2).

Peptides 119. - Peptide Synthesis with N-Carboxy-α-amino Acid Anhydrides

On reaction of N-carboxy-α-amino acid anhydrides (NCA) with equimolar amounts of aminoacids or excess NCA in potassium borate buffer of pH 10.2 (0 deg C) considerable amounts of homooligomers and homopolymers are formed.If an excess of amino acid is used formation of the above mentioned by-products can be suppressed.The extent of homooligomerization and homopolymerization and hydrolysis occurring during the reaction of NCA under the conditions of peptide synthesis is described.