185525-63-7

Basic information

• Product Name: BOC-5-HYDROXY-DL-TRYPTOPHAN
• Synonyms: BOC-5-HYDROXY-DL-TRYPTOPHAN;Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-5-hydroxy-;Boc-DL-5-Hydroxytryptophan
• CAS NO: 185525-63-7
• Molecular Formula: C16H20N2O5
• Molecular Weight: 320.34
• Mol File: 185525-63-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-5-HYDROXY-DL-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-5-HYDROXY-DL-TRYPTOPHAN(185525-63-7)
• EPA Substance Registry System: BOC-5-HYDROXY-DL-TRYPTOPHAN(185525-63-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 185525-63-7(Hazardous Substances Data)

Usage

General Description

BOC-5-HYDROXY-DL-TRYPTOPHAN is a chemical compound that is derived from the amino acid tryptophan. It is a derivative of 5-hydroxytryptophan (5-HTP) and is commonly used in the synthesis of peptides and peptide-based drugs. BOC-5-HYDROXY-DL-TRYPTOPHAN is often used as a protecting group for the amino acid, allowing for selective chemical reactions to occur in peptide synthesis. It is known for its potential applications in the pharmaceutical industry, particularly in the development of drugs targeting the central nervous system and mental health disorders. Additionally, research indicates that BOC-5-HYDROXY-DL-TRYPTOPHAN may have potential therapeutic benefits for a range of medical conditions, including depression, anxiety, and insomnia.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4350-09-8 L-5-HTP 
• 1453-97-0 5-benzyloxygramine 
• 56-69-9 5-hydroxytryptophan 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 53157-48-5 tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate 
• 917372-94-2 (S,S)-[1-[5-(4-amino-phenoxy)-1H-indol-3-ylmethyl]-2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 917373-16-1 (S,S)-{2-(2-cyano-pyrrolidin-1-yl)-1-{5-(4-formyl-phenoxy)-1H-indol-3-ylmethyl}-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917372-91-9 (S,S)-{2-(2-cyano-pyrrolidin-1-yl)-1-[5-(4-nitro-phenoxy)-1H-indol-3-ylmethyl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917373-15-0 (S,S)-{2-(2-carbamoyl-pyrrolidin-1-yl)-1-{5-(4-formyl-phenoxy)-1H-indol-3-ylmethyl}-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917373-17-2 (S,S)-4-{3-[2-tert-butoxycarbonylamino-3-(2-cyano-pyrrolidin-1-yl)-3-oxo-propyl]-1H-indol-5-yloxy}-benzoic acid 
• 917372-90-8 (S,S)-{2-(2-carbamoyl-pyrrolidin-1-yl)-1-[5-(4-nitro-phenoxy)-1H-indol-3-ylmethyl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 917372-95-3 (S,S)-[1-[5-(4-acetylamino-phenoxy)-1H-indol-3-ylmethyl]-2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Highly Efficient Activatable MRI Probe to Sense Myeloperoxidase Activity

Myeloperoxidase (MPO) is a key component of innate immunity but can damage tissues when secreted abnormally. We developed a new generation of a highly efficient MPO-activatable MRI probe (heMAMP) to report MPO activity. heMAMP has improved Gd stability compared to bis-5-HT-Gd-DTPA (MPO-Gd) and demonstrates no significant cytotoxicity. Importantly, heMAMP is more efficiently activated by MPO compared to MPO-Gd, 5HT-DOTA(Gd), and 5HT-DOTAGA-Gd. Molecular docking simulations revealed that heMAMP has increased rigidity via hydrogen bonding intramolecularly and improved binding affinity to the active site of MPO. In animals with subcutaneous inflammation, activated heMAMP showed a 2-3-fold increased contrast-to-noise ratio (CNR) compared to activated MPO-Gd and 4-10 times higher CNR compared to conventional DOTA-Gd. This increased efficacy was further confirmed in a model of unstable atherosclerotic plaque where heMAMP demonstrated a comparable signal increase and responsiveness to MPO inhibition at a 3-fold lower dosage compared to MPO-Gd, further underscoring heMAMP as a potential translational candidate.

MYELOPEROXIDASE IMAGING AGENTS

Provided herein are compounds useful as imaging agents. Exemplary compounds provided herein are useful as myeloperoxidase imaging agents using positron emission tomography or fluorescence imaging techniques. Methods for preparing the compounds provided herein and diagnostic methods using radiolabeled and unlabeled compounds are also provided.

Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines

Quaternary gramines were found to be a suitable source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William's morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields.