4726-96-9

Basic information

• Product Name: O-BENZYL-L-SERINE
• Synonyms: H-ser(Obzl)-OH;O-Benzyl-L-serine >=99.0% (NT);L-Ser(Bzl)-OH;O-Benzyl-L-serine≥ 99% (HPLC);o-(phenylmethyl)-l-serin;O-BENZYL-L-SERINE;SERINE(BZL)-OH;(S)-2-AMINO-3-BENZYLOXYPROPIONIC ACID
• CAS NO: 4726-96-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 225-220-6
• Product Categories: Amino Acid Derivatives;Amino Acids;Amino Acids and Derivatives;Amino Acid Derivatives
• Mol File: 4726-96-9.mol

Chemical Properties

• Melting Point: ~227 °C (dec.)
• Boiling Point: 359℃
• Flash Point: 171℃
• Appearance: White to off-white/Powder
• Density: 1.217
• Vapor Pressure: 8.83E-06mmHg at 25°C
• Refractive Index: 7.3 ° (C=2, 1mol/L HCl)
• Storage Temp.: Store at RT.
• Solubility: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 2.10±0.10(Predicted)
• BRN: 2114846
• CAS DataBase Reference: O-BENZYL-L-SERINE(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-L-SERINE(4726-96-9)
• EPA Substance Registry System: O-BENZYL-L-SERINE(4726-96-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4726-96-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
O-Benzyl-L-Serine is used as a key intermediate in the preparation of serine analogs, which act as specific agonists for N-methyl-D-aspartate (NMDA) receptor glycine binding sites. These agonists play a crucial role in modulating the activity of the NMDA receptor, which is involved in various neurological processes, including learning, memory, and synaptic plasticity. O-BENZYL-L-SERINE's ability to interact with these receptors makes it a promising candidate for the development of therapeutic agents targeting neurological disorders.
Used in Chemical and Analytical Industry:
O-Benzyl-L-Serine also functions as an eluent in ligand exchange chromatography, a technique used for the separation of constrained glutamate receptor ligands. This application is particularly relevant in the field of drug discovery and development, as it aids in the isolation and purification of specific compounds with potential therapeutic properties. O-BENZYL-L-SERINE's effectiveness as an eluent is attributed to its unique chemical properties, which enable it to selectively interact with target molecules and facilitate their separation from complex mixtures.

InChI:InChI=1/C10H13NO3/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m0/s1

Upstream product

• 20806-43-3 Z-Ser(Bzl)-OH 
• 4218-63-7 N-(4-Methoxybenzyloxycarbonyl)-O-benzyl-L-serine 
• 5513-74-6 O-Benzil-N-formil-(S)-(+)-serina 
• 35436-77-2 N-acetyl-O-benzyl-DL-serine 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 5445-44-3 O-benzylserine 
• 20409-07-8 N-Formyl-O-benzyl-DL-serin 
• 23680-31-1 BOC-O-benzyl-L-serine 

Downstream Products

• 46460-82-6 O-benzyl-L-serine methyl ester 
• 20806-43-3 Z-Ser(Bzl)-OH 
• 1581-95-9 O-benzyl-N-trifluoroacetyl-L-serine 
• 5513-74-6 O-Benzil-N-formil-(S)-(+)-serina 
• 58577-87-0 O-benzyl-L-serinol 
• 62061-51-2 (Z)-3-Benzyloxyacrylsaeure 
• 62076-21-5 (S)-2-bromo-3-(phenylmethoxy)propanoic acid 
• 3062-02-0 O-Benzyl-N-chloracetyl-L-serin 
• 19525-87-2 O-methyl O-benzyl-L-serinate hydrochloride 
• 120105-77-3 [2-Benzyloxy-eth-(E)-ylidene]-(6-methoxy-1,4-dimethyl-9H-carbazol-3-ylmethyl)-amine 
• 102249-13-8 N^α,N^G,N^G-tribenzyloxycarbonylarginyl-(O-benzyl)serine 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 127488-83-9 Ser(OBzl)-tetra-n-butyl-ammonium salt 
• 96935-92-1 Z(OMe)-Ser(Bzl)-Ser(Bzl)-OH*DCHA 

Relevant articles and documents

Cinnamic acid derivative with aldose reductase inhibitory activity as well as preparation method and application thereof

The invention discloses a cinnamic acid derivative with aldose reductase inhibitory activity, a preparation method thereof and an application of the cinnamic acid derivative in preparation of a medicine used for treating diabetic complications and diseases caused by oxidative stress. The structure of the compound is shown in a formula I. The preparation method comprises the following steps: firstly reacting substituted benzaldehyde with substituted acetic acid or acid anhydride thereof to obtain substituted cinnamic acid, then reacting with a diamine compound protected by N-tertiary butoxy acyl to obtain substituted cinnamoyl diamide protected by N-tertiary butoxy acyl; and carrying out tertiary butoxy acyl deprotection on the substituted cinnamoyl diamide protected by N-tertiary butoxy acyl, and then reacting with natural or non-natural N-acyl alpha-amino acid, so that the cinnamic acid derivative is obtained. The cinnamic acid derivative compound disclosed by the invention has excellent inhibitory activity on aldose reductase and excellent antioxidant activity and can be applied to preparation of a medicine used for treating the diabetic complications, especially diabetic retinopathy, senile dementia due to diabetes and nerve ending disturbance, as well as diseases caused by the oxidative stress.

Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites

A series of analogues based on serine as lead structure were designed, and their agonist activities were evaluated at recombinant NMDA receptor subtypes (GluN1/2A-D) using two-electrode voltage-clamp (TEVC) electrophysiology. Pronounced variation in subunit-selectivity, potency, and agonist efficacy was observed in a manner that was dependent on the GluN2 subunit in the NMDA receptor. In particular, compounds 15a and 16a are potent GluN2C-specific superagonists at the GluN1 subunit with agonist efficacies of 398% and 308% compared to glycine. This study demonstrates that subunit-selectivity among glycine site NMDA receptor agonists can be achieved and suggests that glycine-site agonists can be developed as pharmacological tool compounds to study GluN2C-specific effects in NMDA receptor-mediated neurotransmission.

POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS

The disclosure provides compounds of the formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables A, R1, and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering to a patient infected with the bacteria, simultaneously or sequentially, a therapeutically effective amount of the antibacterial agent and a compound of formula (I).

Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids

An effective and improved procedure is developed for the synthesis of α-hydroxy carboxylic acids by treatment of the corresponding protonated α-amino acid with tert-butyl nitrite in 1,4-dioxane-water. The amino moiety must be protonated and located α to a carboxylic acid function in order to undergo initial diazotization and successive hydroxylation, since neither β-amino acids nor acid derivatives such as esters and amides undergo hydroxylations. The method is successfully applied for the synthesis of 18 proteinogenic amino acids.

Process improvements for the preparation of kilo quantities of a series of isoindoline compounds

A series of isoindoline analogues with either an indazole (HMR 2934, HMR 2651) or benzisoxazole (HMR 2543) appendage were prepared for the proposed treatment of psychiatric disorders such as obsessive compulsive disorder and attention deficit disorder. The isoindoline compounds were prepared by reduction of the corresponding phthalimides with LiAlH4. One compound was not chiral, and the other two required an enantioselective synthesis. The key step for these optically active analogues involved the coupling by an SN2 process of either a piperazynyl intermediate or a piperdinyl intermediate with methyl 3-benzyloxy-2-trifluoromethansulfonatopropionate. The products for these two analogues had >98% ee. Process improvements led to the multi-kilogram syntheses of each of these compounds.

Amine-boranes: Effective reducing agents for the deracemisation of DL-amino acids using L-amino acid oxidase from Proteus myxofaciens

The deracemisation of DL-α-amino acids using L-amino acid oxidase from Proteus myxofaciens and amine-boranes as chemical reducing agents has been investigated. Amine-boranes were found to be of particular interest in terms of reactivity and chemoselectivity compared to sodium borohydride and cyanoborohydride. Starting from the racemate, a range of D-amino acids were obtained in yields of up to 90% and e.e. >99%.

A novel type of Pd/C-catalyzed hydrogenation using a catalyst poison: Chemoselective inhibition of the hydrogenolysis for O-benzyl protective group by the addition of a nitrogen-containing base

A mild and chemoselective hydrogenation method for a variety of reducible functional groups distinguishing front aliphatic and aromatic' benzyl ethers was accomplished by the addition of an appropriate nitrogen- containing base to the Pd/C-catalyzed hydrogenation system.

2,2-Difluoro-1,3,2-oxazaborolidin-5-ones: Novel approach for selective side-chain protection of serine and threonine

2,2-Difluoro-1,3,2-oxazaborolidin-5-ones 1, which are synthesized from BF3 and salts of amino acids, are highly effective, convenient and, moreover, inexpensive intermediates for the simultaneous protection of both α-amino and α-carboxy groups in α-amino acids. The new method streamlines the hitherto tedious procedures for side-chain protection of Ser and Thr. Ser(Bu′), Thr(Bu′), Ser(Bzl) and Thr(Bzl) are obtained by this procedure in high yields and in pure form using highly reactive reagents.

Acceleration of the N(α)-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1

In solid-phase peptide synthesis, the addition of m-cresol to diluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labile α-amino protecting group, the p-methoxybenzyloxycarbonyl (Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful N(α)-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and N(G)-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.

Certain N-substituted butyramide derivatives

Disclosed are compound of the formula STR1 wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, or each said grouping substituted by lower alkyl; R and Ro independently represent lower alkyl, (C3 -C7)-cycloalkyl-lower alkyl, or aryl-lower alkyl; A represents methylene; or A represents methylene substituted by lower alkyl, by lower alkylthio-lower alkyl, by aryl-lower alkylthio-lower alkyl, by arylthio-lower alkyl, by hydroxy-lower alkyl, by acyloxy-lower alkyl, by lower alkoxy-lower alkyl, by aryl-lower alkyloxy-lower alkyl, by aryloxy-lower alkyl, by amino-lower alkyl, by acylamino-lower alkyl, by guanidino-lower alkyl, by (C3 -C7)-cycloalkyl, by (C3 -C7)-cycloalkyl-lower alkyl, by aryl or aryl-lower alkyl; pharmaceutically acceptable ester and amide derivatives of any said compounds having a free carboxy group; pharmaceutically acceptable salts; methods for synthesis; pharmaceutical compositions thereof; and use thereof as endopeptidase inhibitors.