64410-47-5

Basic information

• Product Name: BOC-TYR-D-ALA-GLY-OH
• Synonyms: BOC-TYR-D-ALA-GLY-OH;N-T-BOC-TYR-D-ALA-GLY;boc-tyr-d-ala-gly;N-(tert-butoxycarbonyl)-Tyr-D-Ala-Gly;(6S,9R)-6-(4-hydroxybenzyl)-2,2,9-trimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oic acid;REF DUPL: Boc-Tyr-D-Ala-Gly-OH;N-[(1,1-Dimethylethoxy)carbonyl]-L-tyrosyl-D-alanylglycine;Boc-Y-D-Ala-G-OH
• CAS NO: 64410-47-5
• Molecular Formula: C₁₉H₂₇N₃O₇
• Molecular Weight: 409.43
• Product Categories: Dipeptides and Tripeptides;Peptides;Tripeptides
• Mol File: 64410-47-5.mol

Chemical Properties

• Melting Point: 146-148℃
• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: BOC-TYR-D-ALA-GLY-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-TYR-D-ALA-GLY-OH(64410-47-5)
• EPA Substance Registry System: BOC-TYR-D-ALA-GLY-OH(64410-47-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64410-47-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
BOC-TYR-D-ALA-GLY-OH is used as a synthetic precursor for the development of peptide-based drugs, facilitating the construction of complex peptide sequences with targeted biological activities. Its selective deprotection and modification capabilities enable the creation of therapeutic peptides with specific functions, such as hormone regulation, enzyme inhibition, or immune response modulation.
Used in Biochemical Research:
In biochemical research, BOC-TYR-D-ALA-GLY-OH is employed as a component in the synthesis of model peptides for studying protein structure, function, and interactions. Its protected structure allows for controlled peptide assembly, providing insights into peptide folding, stability, and binding properties.
Used in Diagnostics and Assays:
BOC-TYR-D-ALA-GLY-OH is utilized in the development of diagnostic tools and assays, where specific peptide sequences are required for the detection or quantification of biological targets. Its versatility in peptide synthesis allows for the creation of probes with high specificity and sensitivity for various diagnostic applications.
Used in Cosmetics and Personal Care:
In the cosmetics and personal care industry, BOC-TYR-D-ALA-GLY-OH is used as a key ingredient in the synthesis of bioactive peptides for anti-aging, skin repair, and other cosmetic applications. Its ability to form specific peptide sequences contributes to the development of products with enhanced efficacy in promoting skin health and appearance.
Used in Agricultural Biotechnology:
BOC-TYR-D-ALA-GLY-OH is employed in the agricultural biotechnology sector for the synthesis of bioactive peptides with potential applications in plant growth regulation, pest control, and disease resistance. Its role in creating specific peptide sequences allows for the development of environmentally friendly and sustainable solutions for crop protection and enhancement.

Upstream product

• 2503-32-4 Z-D-Ala-Gly-OEt 
• 77621-73-9 Boc-Tyr-D-Ala-Gly-OEt 
• 1393358-73-0 C₂₂H₃₁N₃O₇ 
• 1393358-72-9 C₈H₁₄N₂O₃ 
• 74825-83-5 Boc-(L)(α-Me)Tyr-OH 
• 64410-45-3 D-Ala-Gly-OBzl*HCl 
• 67706-13-2 Boc-D-alanine-glycine-OMe 
• 78551-49-2 H-ala-Gly-OMe*HCl 
• 74392-86-2 N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine methyl ester 
• 71591-34-9 N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine 
• 70663-49-9 H-Ala-Gly(OBzl) 
• 64410-44-2 N-(tert-butoxycarbonyl)-D-alanylglycine benzyl ester 
• 50444-70-7 N^α-Boc-D-Ala-Gly-OEt 
• 3978-80-1 Boc-Tyr-OH 

Downstream Products

• 74814-33-8 Boc-Tyr(OH)-D-Ala-Gly-(aminomethyl)cyclobutane 
• 112550-35-3 (S)-2-[(2-{(R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-acetyl)-methyl-amino]-4-methyl-pentanoic acid benzyl ester 
• 74814-30-5 Boc-Tyr(OH)-D-Ala-Gly-2-phenylethylamine 
• 1393358-74-1 C₃₁H₄₆N₄O₈ 
• 1393358-79-6 C₄₃H₅₇N₅O₁₁ 
• 1393358-80-9 C₃₅H₄₅N₅O₉ 
• 1393133-86-2 C₃₈H₄₉N₅O₈ 
• 1393358-75-2 C₂₆H₃₈N₄O₆ 
• 67582-10-9 Boc Tyr D_.Ala Gly Phe OH 
• 96012-25-8 Boc-Tyr-D-Ala-Gly-Phe-Met-NHC₆H₁₃(n) 
• 96012-24-7 Boc-Tyr-D-Ala-Gly-Phe-Met-NHC₃H₇(iso) 
• 96022-24-1 Boc-Tyr-D-Ala-Gly-Phe-Met-NHC₂H₅ 
• 72719-81-4 Tyr-D-Ala-Gly-Phe-Met-NHC₆H₁₃(n) 
• 72719-79-0 Tyr-D-Ala-Gly-Phe-Met-NHC₃H₇(iso) 

Relevant articles and documents

Hydrazone linker as a useful tool for preparing chimeric peptide/ Nonpeptide bifunctional compounds

The area of multitarget compounds, joining two pharmacophores within one molecule, is a vivid field of research in medicinal chemistry. Not only pharmacophoric elements are essential for the design and activity of such compounds, but the type and length o

Factors that restrict the cell permeation of cyclic prodrugs of an opioid peptide, part 3: Synthesis of analogs designed to have improved stability to oxidative metabolism

Previously, our laboratory reported that cyclic peptide prodrugs of the opioid peptide H-Tyr-d-Ala-Gly-Phe-d-Leu-OH (DADLE) are metabolized by cytochrome P450 (CYP450) enzymes, which limits their systemic exposure after oral dosing to animals. In an attempt to design more metabolically stable cyclic prodrugs of DADLE, we synthesized analogs of DADLE cyclized with a coumarinic acid linker (CA; CA-DADLE), which contained modifications in the amino acid residues known to be susceptible to CYP450 oxidation. Metabolic stability and metabolite identification studies of CA-DADLE and its analogs were then compared using rat liver microsomes (RLM), guinea pig liver microsomes (GPLM), and human liver microsomes (HLM), as well as recombinant human recombinant cytochrome P450 3A4 (hCYP3A4). Similar to the results observed for CA-DADLE, incubation of its analogs with RLM, GPLM, and HLM resulted in monohydroxylation of an amino acid side chain on these cyclic prodrugs. When CA-DADLE was incubated with hCYP3A4, similar oxidative metabolism of the peptide was observed. In contrast, incubation of the CA-DADLE analogs with hCYP3A4 showed that these amino-acid-modified analogs are not substrates for this CYP450 isozyme. These results suggest that the amino-acid-modified analogs of CA-DADLE prepared in this study could be stable to metabolic oxidation by CYP3A4 expressed in human intestinal mucosal cells.

Synthesis and biological evaluation of new biphalin analogues with non-hydrazine linkers

Biphalin is a potent opioid peptide agonist, with a palandromic structure, composed of two enkephalin-like active fragments connected tail to tail by a hydrazine linker (Tyr-D-Ala-Gly-Phe-NH-NH-Phe-Gly-D-Ala-Tyr). This study presents the synthesis and

Amino acids and peptides. XXIV. Preparation and antinociceptive effect of [D-Ala2, (N-Me)Phe4]enkephalin analog-poly(ethylene glycol) hybrids

Hybrids of amino-poly(ethylene glycol) (aPEG) and [D-Ala2,(N-Me)Phe4]enkephalin analogs, H-Tyr-D-Ala-Gly-(Me)Phe-aPEG, H-Tyr-D-Ala-Gly-(Me)Phe-Leu-aPEG and H-Tyr-D-Ala-Gly-(Me)Phe-D-Leu-aPEG, were prepared by the solution method and

Investigation of the structural parameters involved in the μ and δ opioid receptor discrimination of linear enkephalin-related peptides

The previous rules proposed for selective recognition of μ and δ opioid receptors by modified enkephalins were investigated through an extensive structure-activity study. Thus, modifications of the sequence of TRIMU 4 (Tyr-D-Ala-Gly-NHCH(CH3)CH

Design and Synthesis of Enkephalin Analogues: Part II - Synthesis of 2, Met5>-Enkephalin Alkylamides Having Morphinomimetic Activity

Alkylamides of 2, Met5>-enkephalin have been synthesized by two different routes.The first method consists of the sequential peptidation of Phe-Met-ONBzl by 2,4,5-trichlorophenyl esters of Boc-Gly, Boc-D-Ala and Boc-Tyr to get

N-Adamantane-substituted tetrapeptide amides

N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.

Synthesis and pharmacological study of some enkephalin analogs in relation to the plurality of opiate receptors

We have synthesized a series of enkephalin analogs and measured their affinity for each type of 'opiate' receptor, the μ receptor and the δ receptor. Furthermore, we have determined their respective antinociceptive activity after intracerebroventricular i