23680-31-1

Basic information

• Product Name: N-BOC-O-Benzyl-L-serine
• Synonyms: N-BOC-O-Benzyl-L-ser;N-Boc-O-benzyl-L-serine Boc-Ser(Bzl)-OH;Boc-Ser(Bz1)-OH;(S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)aMino)propanoic acid;(2S)-3-Benzyloxy-2-(tert-butoxycarbonylamino)propanoic acid;Boc-Ser(Bzl)-OH >=99.0% (T);L-SERINE-N-T-BOC, O-BZ ETHER (15N);L-SERINE-N-T-BOC, O-BZ ETHER (2-13C)
• CAS NO: 23680-31-1
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• EINECS: 245-820-1
• Product Categories: Amino Acids;Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 23680-31-1.mol

Chemical Properties

• Melting Point: 58-60 °C(lit.)
• Boiling Point: 437.02°C (rough estimate)
• Flash Point: 229.7 °C
• Appearance: /Solid
• Density: 1.1454 (rough estimate)
• Vapor Pressure: 4.07E-09mmHg at 25°C
• Refractive Index: 22 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• PKA: 3.53±0.10(Predicted)
• BRN: 3064461
• CAS DataBase Reference: N-BOC-O-Benzyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-O-Benzyl-L-serine(23680-31-1)
• EPA Substance Registry System: N-BOC-O-Benzyl-L-serine(23680-31-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 23680-31-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-O-Benzyl-L-serine is used as a key building block for the synthesis of peptides, which are essential in the development of peptide-based drugs. The growing peptide drug market highlights the importance of this amino acid derivative in creating novel therapeutic agents.
Used in Biotechnology Industry:
In the biotechnology sector, N-BOC-O-Benzyl-L-serine is utilized as a vital component in the synthesis of complex peptide structures. Its application in this field contributes to the advancement of research and development of innovative biotechnological products, including vaccines, enzymes, and other bioactive molecules.
Used in Research and Development:
N-BOC-O-Benzyl-L-serine is also employed in research and development laboratories, where it is used to create and study various peptide sequences. This amino acid derivative aids scientists in understanding the structure-function relationships of peptides and their potential applications in medicine and biotechnology.

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)10-20-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/p-1/t12-/m0/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 5445-44-3 O-benzylserine 
• 3850-40-6 N-Boc-DL-serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4726-96-9 O-Benzyl-L-serine 
• 98015-52-2 1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate 
• 30200-52-3 Boc-Ser(Bzl)-OH*CHA 
• 69871-79-0 (S)-benzyl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoate 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 620-05-3 iodomethylbenzene 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 100-39-0 benzyl bromide 

Downstream Products

• 53261-96-4 3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid vinyl ester 
• 81531-47-7 N--Phe-Pro-Lactam 
• 298713-03-8 N-Boc-O-benzyl-D,L-serine tetradecylamide 
• 851659-32-0 tert-butyl-3-benzyloxy-1-morpholino-1-oxopropan-2-ylcarbamate 

Relevant articles and documents

Aryloxy Triester Phosphoramidates as Phosphoserine Prodrugs: A Proof of Concept Study

The specific targeting of protein-protein interactions by phosphoserine-containing small molecules has been scarce due to the dephosphorylation of phosphoserine and its charged nature at physiological pH, which hinder its uptake into cells. To address these issues, we herein report the synthesis of phosphoserine aryloxy triester phosphoramidates as phosphoserine prodrugs that are enzymatically metabolized to release phosphoserine. This phosphoserine-masking approach was applied to a phosphoserine-containing inhibitor of 14-3-3 dimerization, and the generated prodrugs exhibited improved pharmacological activity. Collectively, this provided a proof of concept that the masking of phosphoserine with biocleavable aryloxy triester phosphoramidate masking groups is a viable intracellular delivery system for phosphoserine-containing molecules. Ultimately, this will facilitate the discovery of phosphoserine-containing small-molecule therapeutics.

Mediating K+/H+ Transport on Organelle Membranes to Selectively Eradicate Cancer Stem Cells with a Small Molecule

Molecules that are capable of disrupting cellular ion homeostasis offer unique opportunities to treat cancer. However, previously reported synthetic ion transporters showed limited value, as promiscuous ionic disruption caused toxicity to both healthy cells and cancer cells indiscriminately. Here we report a simple yet efficient synthetic K+ transporter that takes advantage of the endogenous subcellular pH gradient and membrane potential to site-selectively mediate K+/H+ transport on the mitochondrial and lysosomal membranes in living cells. Consequent mitochondrial and lysosomal damages enhanced cytotoxicity to chemo-resistant ovarian cancer stem cells (CSCs) via apoptosis induction and autophagy suppression with remarkable selectivity (up to 47-fold). The eradication of CSCs blunted tumor formation in mice. We believe this strategy can be exploited in the structural design and applications of next-generation synthetic cation transporters for the treatment of cancer and other diseases related to dysfunctional K+ channels.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders as well as other disorders.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki–Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation

A unique heterogeneous palladium catalyst (7% Pd/WA30) supported on an anion exchange resin, which contains N,N-dimethylaminoalkyl functionalities on the polymer backbone, was developed. 7% Pd/WA30 could smoothly catalyze Suzuki–Miyaura reactions of even less reactive heteroaryl chlorides and heteroarylboronic acids to afford various (hetero)biaryls due to the electron-donating effect of the tert-amines on WA30 to Pd species. It was also applicable as a chemoselective hydrogenation catalyst, showing inactivity for the hydrogenolysis of tert-butyldimethylsilyl (TBS) ethers, alkyl benzyl ethers, and benzyl alcohols. The tert-amines on WA30 acted as moderate catalyst poisons for Pd, resulting in chemoselective hydrogenation. 7% Pd/WA30 was reused for at least five times without any loss of the hydrogenation catalytic activity. (Figure presented.).

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMD A receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Novel branched isocyanides as useful building blocks in the Passerini-amine deprotection-acyl migration (PADAM) synthesis of potential HIV-1 protease inhibitors

Novel branched isocyanides have been prepared from l-serine and used as building blocks in the Passerini-amine deprotection-acyl migration (PADAM) sequence for the preparation of compounds with activity against HIV-1 protease.

CATHEPSIN S INHIBITORS

Cathepsin S inhibitors having formula (I), (II), (III) or (IV) as shown in the specification. These inhibitors can be used to treat cancer and autoimmune/inflammatory diseases.

Design and synthesis of α-ketoamides as cathepsin s inhibitors with potential applications against tumor invasion and angiogenesis

A series of small molecules bearing an α-ketoamide warhead were synthesized and evaluated for their ability to inhibit cathepsin S, a key proteolytic enzyme upregulated in many cancers during tumor progression and metastasis. Most of the synthetic compounds were noncytotoxic, but several robustly inhibited cathepsin S (IC50 10 nM) and potently suppressed cell migration, invasion, and capillary tube formation. These results highlight the potential of α-ketoamide therapy for preventing or delaying cancer spread.

PYRROLOPYRROLONES ACTIVE AS KINASE INHIBITORS

Compounds represented by formula (I) wherein A, R1, R2, R3, and R4 are as defined in the specification, compositions thereof, and methods of use thereof.