10433-52-0

Basic information

• Product Name: O-BENZYL-D-SERINE
• Synonyms: D-SERINE BENZYL ETHER;D-SERINE(BZL)-OH;H-D-SER(BZL)-OH;O-BENZYL-D-SERINE;(R)-2-AMINO-3-BENZYLOXYPROPIONIC ACID;(R)-2-Amino-3-Benzyloxypropionic acid,O-Benzyl-D-serine;(R)-2-Amino-3-(benzyloxy)propanoic acid;O-(Phenylmethyl)-D-serine
• CAS NO: 10433-52-0
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 233-916-6
• Mol File: 10433-52-0.mol

Chemical Properties

• Melting Point: ~227 °C (dec.)
• Boiling Point: 359.053 °C at 760 mmHg
• Flash Point: 170.949 °C
• Appearance: /
• Density: 1.217
• Vapor Pressure: 8.83E-06mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Store at 0-5°C
• PKA: 2.10±0.10(Predicted)
• BRN: 2649409
• CAS DataBase Reference: O-BENZYL-D-SERINE(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-D-SERINE(10433-52-0)
• EPA Substance Registry System: O-BENZYL-D-SERINE(10433-52-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 10433-52-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
O-Benzyl-D-serine is used as an intermediate in the synthesis of pharmaceuticals for its ability to be efficiently converted from D-5-monosubstituted hydantoin by E.coli. This conversion process reveals three co-expressed genes encoding hydantoin racemase, D-hydantoinase, and N-carbamoyl-D-amino acid amidohydrolase, which are crucial for its production and potential therapeutic applications.
Used in Chemical Synthesis:
O-Benzyl-D-serine is used as a building block in the chemical synthesis of various organic compounds, taking advantage of its unique structure and reactivity. Its benzyl-protected serine moiety allows for selective reactions and the synthesis of complex molecules with potential applications in different industries.
Used in Research and Development:
In the field of research and development, O-Benzyl-D-serine serves as a valuable compound for studying enzyme mechanisms, exploring the scope of asymmetric synthesis, and developing new methodologies for the synthesis of biologically active molecules. Its unique properties make it an attractive candidate for probing enzyme selectivity and catalytic activity.
Used in Enzyme Inhibition Studies:
O-Benzyl-D-serine can be used in enzyme inhibition studies, particularly for enzymes that utilize D-serine as a substrate or inhibitor. Its modified structure allows researchers to investigate the binding preferences and specificity of enzymes, contributing to a better understanding of enzyme function and the development of enzyme-targeted therapies.
Overall, O-Benzyl-D-serine is a multifaceted compound with applications spanning across the pharmaceutical, chemical synthesis, research and development, and enzyme inhibition fields. Its unique properties and synthetic versatility make it a valuable asset in the development of new drugs, materials, and methodologies.

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-/m1/s1

Upstream product

• 1233494-98-8 (R)-O-Benzylserine hydrochloride 
• 5445-44-3 O-benzylserine 
• 3587-60-8 Benzyloxymethyl chloride 
• 84907-81-3 (2R)-3-benzyloxy-2-aminopropanoic acid methyl ester 
• 84907-79-9 (3R,6S)-3-Benzyloxymethyl-2,5-dimethoxy-6-isopropyl-3,6-dihydropyrazine 
• 84907-80-2 (3S,6R)-6-Benzyloxy-2,5-dimethoxy-3-(3,4-dimethoxybenzyl)-3-methyl-3,6-dihydropyrazine 
• 20409-07-8 N-Formyl-O-benzyl-DL-serin 
• 100-39-0 benzyl bromide 
• 47173-80-8 N-Boc-D-serine(Bzl)-OH 

Downstream Products

• 58578-42-0 (2S)-3-benzyloxy-2-<(benzyloxycarbonyl)amino>propanol 
• 133406-42-5 N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipoyl-O-benzyl-D-serine 
• 20806-42-2 (R)-N-benzyloxycarbonyl-O-benzyl serine 
• 124593-82-4 (R)-3-Benzyloxy-2-[(S)-2-(2-phenoxy-acetylamino)-pent-4-enoylamino]-propionic acid methyl ester 
• 47173-80-8 N-Boc-D-serine(Bzl)-OH 
• 192723-38-9 methanesulfonyl-D-Ser(Bn) 
• 240428-54-0 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-O-(phenylmethyl)-D-serine 
• 226699-20-3 (R)-N-benzyloxycarbonyl O-benzyl serinamide 
• 192723-32-3 (R)-3-Benzyloxy-N-((S)-1-hydroxymethyl-2-phenyl-ethyl)-2-methanesulfonylamino-propionamide 
• 81306-86-7 N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipoyl-O-benzyl-D-serinyl-D-valine benzylester 
• 58578-51-1 (Z)-(S)-4-((R)-3-Benzyloxy-2-benzyloxycarbonylamino-propoxy)-2-benzyloxycarbonylamino-but-3-enoic acid benzyl ester 
• 58578-50-0 (E)-(S)-4-((R)-3-Benzyloxy-2-benzyloxycarbonylamino-propoxy)-2-benzyloxycarbonylamino-but-3-enoic acid benzyl ester 
• 159634-89-6 (R)-3-Benzyloxy-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-propionic Acid 
• 1026087-20-6 3(R)-benzyloxy-2-(2-tert-butoxycarbonylamino-2-methyl-propionyl-amino)-propionic acid 

Relevant articles and documents

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%.

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.

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.