13171-93-2

Basic information

• Product Name: Z-GLY-GLY-PHE-OH
• Synonyms: Z-GLYCYL-GLYCYL-L-PHENYLALANINE;Z-GLY-GLY-PHE-OH;N-cbz-gly-gly-phe;N-carbobenzyloxy-Gly-Gly-Phe
• CAS NO: 13171-93-2
• Molecular Formula: C₂₁H₂₃N₃O₆
• Molecular Weight: 413.42
• Mol File: 13171-93-2.mol

Chemical Properties

• Boiling Point: 771.2 °C at 760 mmHg
• Flash Point: 420.2 °C
• Appearance: /
• Density: 1.301 g/cm³
• Vapor Pressure: 5.08E-25mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: -15°C
• PKA: 3.50±0.10(Predicted)
• CAS DataBase Reference: Z-GLY-GLY-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLY-GLY-PHE-OH(13171-93-2)
• EPA Substance Registry System: Z-GLY-GLY-PHE-OH(13171-93-2)

Safety Data

• Hazardous Substances Data: 13171-93-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Z-GLY-GLY-PHE-OH is used as a model compound for studying peptide synthesis, structure-activity relationships, and enzyme kinetics. Its well-defined structure and properties make it an ideal candidate for understanding the fundamental aspects of peptide chemistry and biology.
Used in Drug Delivery Systems:
Z-GLY-GLY-PHE-OH is used as a carrier molecule in drug delivery systems to improve the solubility, stability, and bioavailability of therapeutic agents. Its small size, water solubility, and ease of modification with functional groups make it a versatile platform for the development of targeted drug delivery systems.
Used in Protease Inhibition:
Z-GLY-GLY-PHE-OH is used as a substrate or inhibitor in the study of protease enzymes. Its specific amino acid sequence can be designed to interact with specific proteases, providing insights into enzyme specificity, kinetics, and mechanisms of action.
Used in Peptide-based Drug Development:
Z-GLY-GLY-PHE-OH is used as a building block or template in the development of peptide-based drugs. Its small size, solubility, and ease of modification make it an attractive candidate for the design of novel therapeutic peptides with improved pharmacokinetic properties and biological activities.
Used in Biochemical Assays and Diagnostics:
Z-GLY-GLY-PHE-OH is used as a reagent or standard in various biochemical assays and diagnostic tests. Its well-defined structure and properties make it suitable for the development of assays to measure enzyme activity, protein-protein interactions, and other biological processes.

InChI:InChI=1/C21H23N3O6/c25-18(12-23-21(29)30-14-16-9-5-2-6-10-16)22-13-19(26)24-17(20(27)28)11-15-7-3-1-4-8-15/h1-10,17H,11-14H2,(H,22,25)(H,23,29)(H,24,26)(H,27,28)

Upstream product

• 15027-03-9 Z-Gly-Gly-L-Phe-OMe 
• 10466-61-2 (2S)-amino-4-methylpentanamide hydrochloride 
• 2566-19-0 CbzGlyGly 
• 2899-60-7 Cbz-Gly-ONSuc 
• 32943-08-1 Cbz-Gly-Gly-OSucc 
• 63-91-2 L-phenylalanine 
• 252846-38-1 Z-Gly-Gly-L-Phe-OCam 
• 169676-30-6 Z-Gly-Gly-L-Phe-OCH₂CF₃ 
• 501-53-1 benzyl chloroformate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 13437-63-3 methyl [({[(benzyloxy)carbonyl]amino}acetyl)amino]acetate 

Downstream Products

• 68835-85-8 N-benzyloxycarbonyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester 
• 69983-47-7 N-Cbz-Gly-Gly-Phe-Leu-OH 
• 68709-94-4 glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester 
• 60254-83-3 [des-tyr¹]-leucine enkephalin 
• 77426-95-0 Z-Gly-Gly-Phe-Leu-O-t-butyl 
• 75720-16-0 1-O-(N-acetylglycylglycyl-L-phenylalanyl)-β-D-glucopyranose 
• 75720-13-7 1-O-(glycylglycyl-L-phenylalanyl)-β-D-glucopyranose 
• 75719-93-6 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-D-phenylalanyl)-β-D-glucopyranose 
• 75719-90-3 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L,D-phenylalanyl)-α-D-glucopyranose 
• 75719-90-3 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L,D-phenylalanyl)-β-D-glucopyranose 
• 75720-14-8 1-O-(glycylglycyl-L-phenylalanyl)-β-D-glucopyranose trifluoroacetate 
• 75720-14-8 1-O-(glycylglycyl-L-phenylalanyl)-α-D-glucopyranose trifluoroacetate 
• 75720-15-9 2,3,4,6-tetra-O-acetyl-1-O-(N-acetylglycylglycyl-L-phenylalanyl)-β-D-glucopyranose 
• 75719-92-5 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L-phenylalanyl)-β-D-glucopyranose 

Relevant articles and documents

Quickly released antibody drug conjugate

The invention discloses an antibody drug conjugate or a pharmaceutically acceptable salt thereof. The brand-new quickly released antibody drug conjugate is used for treating tumors or other diseases,and the antibody drug conjugate is particularly suitable for a situation that a drug molecular structure contains hydroxyl groups, and has high stability and good water solubility in internal circulation.

Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent

Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 ± 1.10 × 104 M-1 and ΔG of -100.3 kJ mol-1 in comparison to a Ka 0.41 × 103 ± 0.09 M-1 and ΔG of -19.2 ± 0.06 kJ mol-1 for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg-1 dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.

α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach using carbamoylmethyl esters as acyl donors in organic media

The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach is demonstrated in several model systems carried out in organic media with low water content. Furthermore, this approach is successfully applied to the construction of the Leu-enkephalin sequence via a 4 + 1 segment coupling.

Inhibitors of tripeptidyl peptidase II. 2. Generation of the first novel lead inhibitor of cholecystokinin-8-inactivating peptidase: A strategy for the design of peptidase inhibitors

The cholecystokinin-8 (CCK-8)-inactivating peptidase is a serine peptidase which has been shown to be a membrane-bound isoform of tripeptidyl peptidase II (EC 3.4.14.10). It cleaves the neurotransmitter CCK-8 sulfate at the Met-Gly bond to give Asp-Tyr(SO3H)-Met-OH + Gly-Trp-Met-Asp-Phe-NH2. In seeking a reversible inhibitor of this peptidase, the enzymatic binding subsites were characterized using a fluorimetric assay based on the hydrolysis of the artificial substrate Ala-Ala-Phe-amidomethylcoumarin. A series of di- and tripeptides having various alkyl or aryl side chains was studied to determine the accessible volume for binding and to probe the potential for hydrophobic interactions. From this initial study the tripeptides Ile-Pro-Ile-OH (K(i) = 1 μM) and Ala-Pro-Ala-OH (K(i) = 3 μM) and dipeptide amide Val-Nvl-NHBu (K(i) = 3 μM) emerged as leads. Comparison of these structures led to the synthesis of Val-Pro-NHBu (K(i) = 0.57 μM) which served for later optimization in the design of butabindide, a potent reversible competitive and selective inhibitor of the CCK-8-inactivating peptidase. The strategy for this work is explicitly described since it illustrates a possible general approach for peptidase inhibitor design.

Superiority of the carbamoylmethyl ester as an acyl donor for the protease-catalyzed kinetically controlled peptide synthesis in organic media: Application to segment condensations

The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalyzed kinetically controlled peptide synthesis was demonstrated in several segment condensations carried out in organic media with low water content. Then this approach was successfully applied to the construction of the Leuenkephalin sequence via the 4 + 1 segment condensation.