132622-69-6

Basic information

• Product Name: (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID
• Synonyms: (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID;(R)-1-BOC-4-AMINO-L-PROLINE;(R)-N-BOC-4-AMINO-L-PROLINE;N-BOC-TRANS-4-AMINO-L-PROLINE;(2S,4R)-4-Aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;(4R)-4-amino-1-(tert-butoxycarbonyl)-L-proline(SALTDATA: FREE);(2S,4R)-1-BOC-4-ANINO-PYRROLIDINE-2-CARBOXYLIC ACID;(4R)-1-Boc-4-amino-L-proline
• CAS NO: 132622-69-6
• Molecular Formula: C₁₀H₁₈N₂O₄
• Molecular Weight: 230.26
• Mol File: 132622-69-6.mol

Chemical Properties

• Melting Point: 228-229 °C(Solv: ethanol (64-17-5))
• Boiling Point: 371.1 °C at 760 mmHg
• Flash Point: 178.2 °C
• Appearance: /
• Density: 1.232 g/cm³
• Refractive Index: 1.516
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.65±0.20(Predicted)
• CAS DataBase Reference: (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID(132622-69-6)
• EPA Substance Registry System: (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID(132622-69-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 132622-69-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID is used as a building block for the development of pharmaceutical agents due to its unique structure and the presence of a BOC protecting group, which facilitates the synthesis of complex molecules with controlled reactivity.
Used in Peptide Synthesis:
In the field of peptide synthesis, (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID serves as a key component, providing a protected amino acid that can be selectively deprotected and incorporated into peptide chains, enhancing the efficiency and selectivity of the synthesis process.
Used in Medicinal Chemistry:
(2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID is utilized as a versatile compound in medicinal chemistry for the design and synthesis of novel drug candidates, capitalizing on its unique stereochemistry and functional groups to explore new therapeutic agents.
Used in Drug Discovery:
In drug discovery, (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID is employed as a starting material or intermediate in the synthesis of potential drug molecules, leveraging its chemical properties and reactivity to create new compounds with therapeutic potential.

InChI:InChI=1/C10H18N2O4/c1-10(2,3)16-9(15)12-5-6(11)4-7(12)8(13)14/h6-7H,4-5,11H2,1-3H3,(H,13,14)/t6-,7+/m1/s1

Upstream product

• 185304-19-2 (2S,4R)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate 
• 132622-68-5 (2S,4R)-4-azido-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 176486-63-8 (2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 37813-30-2 (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 132623-04-2 (4R)-1-(tert-butoxycarbonyl)-4-azido-L-proline ethyl ester 
• 132622-64-1 (4S)-1-(tert-butoxycarbonyl)-4-chloro-L-proline ethyl ester 
• 874162-95-5 (2S,4S)-1-(tert-butoxycarbonyl)-4-bromoproline benzyl ester 

Downstream Products

• 874163-05-0 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 
• 874163-03-8 methyl 3(R)-[(4(R)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate 
• 874163-09-4 3(R)-[(4(R)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 
• 874163-10-7 3(R)-[(4(R)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 
• 874163-11-8 3(R)-[(4(R)-((4-azido-2-hydroxy-5-iodobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide 
• 609-36-9 rac-Pro-OH 
• 273222-05-2 N-Fmoc-trans-(2S,4R)-4-(N-allyloxycarbonyl)amino-L-proline 
• 176486-63-8 (2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 132622-70-9 (4R)-1-(tert-butoxycarbonyl)-4-<<<(p-toluenesulfonyl)imino>aminomethyl>amino>-L-proline 
• 874163-00-5 (2S,4R)-1-(tert-butoxycarbonyl)-4-(N-benzyloxycarbonyl)aminoproline 

Relevant articles and documents

Structure - Activity relationship studies of targeting ligands against breast cancer cells

A series of LXY3 (1) analogues were designed and synthesized. Their binding affinity was demonstrated using MDA-MB-231 breast cancer cells adherence inhibition assay. Further structure-activity relationship was obtained. Analogue 29 was discovered to have 3.5-fold increase of the binding affinity. Fluorescent microscopy and in vivo and ex vivo imaging studies demonstrated that 29 is an efficient in vivo targeting agent against α3 integrin of MDA-MB-231 breast tumor xenograft implant. 2009 American Chemical Society.

Inhibitors of Hepatitis C Virus

Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Inhibitors of Hepatitis C Virus

Macrocyclic peptides are disclosed having the general formula: wherein R3, R′3, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Discovery of subnanomolar arginine-glycine-aspartate-based αvβ3/αvβ5 integrin binders embedding 4-aminoproline residues

The embodiment of 4-aminoproline residues (Amp) into the arginine-glycine-aspartate (RGD) sequence led to the discovery of a novel class of high-affinity αvβ3/αvβ 5 integrin binders [IC50h(αvβ 3) 0.03-5.12 nM; IC50h(αvβ 5) 0.88-154 nM]. A total of eight cyclopeptides of type cyclo-[-Arg-Gly-Asp-Amp-], 5-12, were assembled by a standard solid-phase peptide synthesis protocol that involved the C2-carboxyl and C4-amino functionalities of the proline scaffolds, leaving the Nα- nuclear site untouched. Functionalization of this vacant proline site with either alkyl or acyl substituents proved feasible, with significant benefit to the integrin binding capabilities of the ligands. Notably, six out of eight cyclopeptide inhibitors, 5-7 and 9-11, showed moderate yet significant selectivity toward the αvβ3 receptor. The three-dimensional structure in water was determined by NMR techniques and molecular dynamics calculations. Docking studies to the X-ray crystal structure of the extracellular segment of integrin αvβ3 complexed with reference compound 1 were also performed on selected analogues to highlight the structural features required for potent ligand binding affinity.

Hepatitis C virus inhibitors

Macrocyclic peptides are disclosed having the general formula: wherein R′, R3, R3′, R4, R6, X, Q, and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor

Pro-Leu-Gly-NH2 (PLG), in addition to its endocrine effects, possesses the ability to modulate dopamine 02 receptors within the central nervous system. However, the precise binding site of PLG is unknown. Potential photoaffinity-labeling ligand

HEPATITIS C VIRUS INHIBITORS

Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

Chimeric amino acid analogues

A chimeric amino acid analogue is provided suitable for incorporating into peptides which compound is represented by Formula 1: STR1 where P1 is preferably an amine protecting agent, and P2 and P3 are preferably amine or guanidine protecting agents. X can be OH, halide, or preferably an activating group suitable for conjugating the compound of Formula 1 to a peptide by conventional means, and m and n are 0-1 and 0-2 respectively. Peptides containing the chimeric amino acid analog are provided and include a platelet-aggregation inhibitor represented by where Aaa1 is Gly or H, Cpdl is the compound of Formula 1 which has been deprotected and Aaa2 is a hydrophobic amino acid preferably Val.

Conformationally Restricted Arginine Analogues

We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues.These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the co