119768-45-5

Basic information

• Product Name: BOC-5-HYDROXY-L-TRYPTOPHAN
• Synonyms: BOC-TRP(5-OH)-OH;BOC-5-HYDROXY-L-TRYPTOPHAN;BOC-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID;BOC-L-5-HYDROXYTRYPTOPHAN;Nα-Boc-5-hydroxy-L-tryptophan;L-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-5-hydroxy-;Nα-Boc-5-hydroxy-L-tryptophan≥ 97% (HPLC)
• CAS NO: 119768-45-5
• Molecular Formula: C₁₆H₂₀N₂O₅
• Molecular Weight: 320.34
• Mol File: 119768-45-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-5-HYDROXY-L-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-5-HYDROXY-L-TRYPTOPHAN(119768-45-5)
• EPA Substance Registry System: BOC-5-HYDROXY-L-TRYPTOPHAN(119768-45-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 119768-45-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

Uses

Boc-5-hydroxy-L-tryptophan is a related compound of the amino acid L-Tryptophan (CAT# T947210). It can be used in the synthesis of tryptophan-derived butyrylcholinesterase inhibitors as anti-Alzheimer''s agents. It can also be useful in the design of compounds recognized by the L-type amino acid transporter 1.

Upstream product

• 1453-97-0 5-benzyloxygramine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4350-09-8 L-5-HTP 

Downstream Products

• 179669-45-5 (S)-2-Benzyloxycarbonylamino-6-[(S)-2-tert-butoxycarbonylamino-3-(5-hydroxy-1H-indol-3-yl)-propionylamino]-hexanoic acid methyl 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 
• 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 
• 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 
• 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 
• 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 
• 917373-16-1 (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 
• 917372-94-2 (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 
• 53157-48-5 tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate 
• 85676-39-7 H-5HTP-Har-OMe_.2Tos 
• 496840-02-9 2-[2-tert-butoxycarbonylamino-3-(5-hydroxy-1H-indol-3-yl)-propionylamino]-3-phenyl-propionic acid 

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.

Quantitative insight into the design of compounds recognized by the L-type amino acid transporter 1 (LAT1)

L-Type amino acid transporter 1 (LAT1) is a transmembrane protein expressed abundantly at the blood-brain barrier (BBB), where it ensures the transport of hydrophobic acids from the blood to the brain. Due to its unique substrate specificity and high expression at the BBB, LAT1 is an intriguing target for carrier- mediated transport of drugs into the brain. In this study, a comparative molecular field analysis (CoMFA) model with considerable statistical quality (Q2=0.53, R2=0.75, Q2 SE=0.77, R2 SE=0.57) and good external predictivity (CCC=0.91) was generated. The model was used to guide the synthesis of eight new prodrugs whose affinity for LAT1 was tested by using an in situ rat brain perfusion technique. This resulted in the creation of a novel LAT1 prodrug with l-tryptophan as the promoiety; it also provided a better understanding of the molecular features of LAT1-targeted high-affinity prodrugs, as well as their promoiety and parent drug. The results obtained will be beneficial in the rational design of novel LAT1-binding prodrugs and other compounds that bind to LAT1.