98266-33-2

Basic information

• Product Name: (R)-N-Boc-(3-Pyridyl)alanine
• Synonyms: BOC-D-3-PYRIDYLALANINE 98%;N-tert-Butoxycarbonyl-D-3-(3-Pyridyl) Alanine;3-Pyridin-3-yl-D-alanine, N-BOC protected;(R)-2-(tert-butoxycarbonylamino)-3-(pyridin-3-yl)propanoic acid;N-BOC-(3-PYRIDYL)ALANINE;(R)-N-BOC-(3-PYRIDYL)ALANINE, 95%, 98% EE;(R)-N-BOC-(3-Pyridyl)alanine, 98% ee;(R)-N-BOC-(3-Pyridyl)alanineN-tert-Butoxycarbonyl-3-pyridyl-D-alanine
• CAS NO: 98266-33-2
• Molecular Formula: C₁₃H₁₈N₂O₄
• Molecular Weight: 266.29
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Pyridine series;Amino Acid Derivatives;Unusual Amino Acids;a-amino
• Mol File: 98266-33-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 136.8 °C
• Boiling Point: 409.5°C (rough estimate)
• Flash Point: 227.7 °C
• Appearance: off-white powder
• Density: 1.1738 (rough estimate)
• Vapor Pressure: 5.43E-09mmHg at 25°C
• Refractive Index: 1.6450 (estimate)
• Storage Temp.: Store at RT.
• PKA: 3.43±0.10(Predicted)
• CAS DataBase Reference: (R)-N-Boc-(3-Pyridyl)alanine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Boc-(3-Pyridyl)alanine(98266-33-2)
• EPA Substance Registry System: (R)-N-Boc-(3-Pyridyl)alanine(98266-33-2)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 98266-33-2(Hazardous Substances Data)

Usage

Description

(R)-N-Boc-(3-Pyridyl)alanine, also known as Boc-D-3-pyridylalanine, is an alanine derivative characterized by the presence of a 3-pyridyl group attached to the alanine molecule. The Boc (tert-butyloxycarbonyl) group serves as a protecting group for the amino function, allowing for selective reactions to occur at other sites on the molecule. This chiral compound exhibits a specific (R)-configuration, which is crucial for its applications in various chemical and biological processes.

Uses

Used in Chemical Synthesis:
(R)-N-Boc-(3-Pyridyl)alanine is used as a building block in the synthesis of complex organic molecules, particularly those with chiral centers. Its unique structure allows for the creation of enantiomerically pure compounds, which are essential in many pharmaceutical and agrochemical applications.
Used in Peptide Chemistry:
In the field of peptide chemistry, (R)-N-Boc-(3-Pyridyl)alanine is utilized as a non-natural amino acid for the synthesis of novel peptides with specific biological activities. The incorporation of this amino acid into peptide sequences can lead to the development of new therapeutic agents, such as antibiotics, antiviral agents, and anticancer drugs.
Used in Pharmaceutical Development:
(R)-N-Boc-(3-Pyridyl)alanine is used as a key intermediate in the development of pharmaceutical compounds. Its unique structural features enable the design of drugs with improved selectivity, potency, and reduced side effects. The chiral nature of this compound ensures that only the desired enantiomer is synthesized, which is crucial for the safety and efficacy of the final drug product.
Used in Agrochemical Research:
In agrochemical research, (R)-N-Boc-(3-Pyridyl)alanine is employed as a starting material for the synthesis of chiral pesticides and herbicides. The use of this compound allows for the development of more effective and environmentally friendly agrochemicals by targeting specific pests or weeds while minimizing harm to non-target organisms.
Overall, (R)-N-Boc-(3-Pyridyl)alanine is a versatile compound with a wide range of applications in various industries, including pharmaceuticals, agrochemicals, and chemical synthesis. Its unique structure and chiral properties make it an invaluable tool for the development of new and improved products in these fields.

InChI:InChI=1/C13H18N2O4/c1-13(2,3)19-12(18)15-10(11(16)17)7-9-5-4-6-14-8-9/h4-6,8,10H,7H2,1-3H3,(H,15,18)(H,16,17)/p-1/t10-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 70702-47-5 (2R)-2-amino-3-(pyridin-3-yl)propanoic acid 
• 500-22-1 3-pyridinecarboxaldehyde 
• 102913-22-4 (4Z)-2-methyl-4((pyridin-3-yl)methylene)oxazol-5(4H)-one 
• 170092-30-5 N-acetyl-(β-3-pyridyl)-DL-alanine 
• 89890-92-6 N-acetyl-(β-3-pyridyl)-α,β-dehydroalanine 

Downstream Products

• 128718-99-0 N-tert-butoxycarbonyl-D-3-pyridylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester 
• 197088-84-9 (R)-3-(3-pyridyl)alanine methyl ester dihydrochloride 
• 112568-12-4 antide 

Relevant articles and documents

CHEMICAL COMPOUNDS

The present disclosure relates to compounds of Formula (I): and to their pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein inhibit the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inter alia autoinflammatory and autoimmune diseases and cancers.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

New Effective Gonadotropin Releasing Hormone Antagonists with Minimal Potency for Histamine Release in Vitro

In order to minimize the adverse effect of histamine release in the rat of some gonadotropin releasing hormone (GnRH) antagonists, such as 1,D4FPhe2,DTrp3,DArg6>-GnRH, new structures with modifications at positions 1, 2, 3, 5, 6, 7, and 10 were synthesized and tested in several biological systems.In vitro: the affinity for the pituitary GnRH receptor was measured as was the ability of the analogues to inhibit GnRH-stimulated release of luteinizing hormone (LH) by dispersed anterior pituitary cells in culture and to release histamine from rat mast cells.In vivo: inhibition of ovulation in the cycling rat was determined after subcutaneous (sc) injection of the peptides at noon on the day of proestrus; the duration of action of the peptides was evaluated by measuring LH levels in the castrated male rat after sc injection of some selected analogues. 1,D4ClPhe2,D3Pal3,Arg5,D-4-p-methoxybenzoyl-2-aminobutyric acid6,DAla10>-GnRH was found to be one of the most potent analogues of this series, causing a 100percent inhibition of ovulation at 5 μg/kg or less.Release of histamine was observed at doses 10-25 times required for 1,D4Phe2,DTrp3,DArg6>-GnRH.Thus, introduction of arginine in position 5 with a hydrophobic amino acid in position 6 is compatible with high potency in several biological systems and results in compounds with lowered potency to release histamine compared to homologous peptides with tyrosine in position 5 and D-arginine in position 6.