101555-60-6

Basic information

• Product Name: BOC-D-BETA-HOMOPROLINE
• Synonyms: RARECHEM AK PT F109;(R)-2-CARBOXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;BOC-D-BETA-HOMOPROLINE;Boc-D-b-HoPro-OH;(R)-2-(Carboxymethyl)pyrrolidinium chloride;(R)-Pyrrolidine-2-acetic acid hydrochloride;(R)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid;Boc-D-beta-HoPro-OH
• CAS NO: 101555-60-6
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 165.62
• Product Categories: Beta amino acids
• Mol File: 101555-60-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 303°C at 760 mmHg
• Flash Point: 137.1°C
• Appearance: /
• Density: 1.151±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.000221mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 4.56±0.10(Predicted)
• CAS DataBase Reference: BOC-D-BETA-HOMOPROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-BETA-HOMOPROLINE(101555-60-6)
• EPA Substance Registry System: BOC-D-BETA-HOMOPROLINE(101555-60-6)

Safety Data

• Hazardous Substances Data: 101555-60-6(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

InChI:InChI=1/C6H11NO2.ClH/c8-6(9)4-5-2-1-3-7-5;/h5,7H,1-4H2,(H,8,9);1H/t5-;/m1./s1

Upstream product

• 201039-13-6 (R)-2-cyanomethyl pyrrolidine-1-carboxylic acid, tert-butyl ester 
• 128510-88-3 tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 61350-65-0 (R)-2-(pyrrolidin-2-yl)acetic acid 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 118758-56-8 tert-butyl 2-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate 
• 439918-59-9 (R)-2-(pyrrolidin-2-yl)acetic acid hydrochloride salt 
• 152665-79-7 (R)-tert-butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate 

Downstream Products

• 1314696-17-7 tert-butyl (2R)-2-(2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxoethyl)pyrrolidine-1-carboxylate 
• 1314696-19-9 tert-butyl (2R)-2-(2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl)pyrrolidine-1-carboxylate 
• 1314696-20-2 1-(2-((2R)-1-[(4-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-21-3 1-(2-((2R)-1-[(2-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-23-5 4-methyl-1-(2-((2R)-1-[(4-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperidine 
• 1314696-26-8 4-methyl-1-(2-((2R)-1-[(2-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperidine 
• 1314696-28-0 1-(2-((2R)-1-[(4-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 
• 1314696-32-6 1-(2-((2R)-1-[(2-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 
• 1314696-33-7 1-(2-methoxyphenyl)-4-(2-((2R)-1-[(4-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperazine 
• 1314696-35-9 1-(2-methoxyphenyl)-4-(2-((2R)-1-[(2-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperazine 
• 1314696-36-0 1-(2-((2R)-1-[(4-[⁽¹⁸⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-37-1 1-(2-((2R)-1-[(2-[⁽¹⁸⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-40-6 1-(2-((2R)-1-[(4-[⁽¹⁹⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 
• 1314696-41-7 1-(2-((2R)-1-[(2-[⁽¹⁹⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 

Relevant articles and documents

Enzymatic resolution of cyclic N-Boc protected β-aminoacids

Methyl and ethyl esters of N-Boc homoproline, homopipecolic acid and 3-carboxymethyl-morpholine were kinetically resolved by hydrolysis catalysed by Burkholderia cepacia lipase to give the corresponding acids and residual esters in enantiomeric excesses better than 99% (E > 100).

Synthesis and Stereochemical Assignment of Conioidine A: DNA- And HSA-Binding Studies of the Four Diastereomers

Conioidine A (1), isolated in 1993 with unknown relative and absolute configuration, was suggested to be a DNA-binding compound by an indirect technique. Four stereoisomers of conioidine A have been synthesized from d- and l-proline, and the natural product has been identified as possessing (4R,6R) absolute configuration. Binding of the conioidine diastereomers to calf thymus DNA (CT DNA) and human serum albumin (HSA) has been investigated by fluorescence spectroscopy and isothermal titration calorimetry (ITC). All stereoisomers display at least an order of magnitude weaker binding to DNA than the control compound netropsin; however, a strong association with HSA was observed for the (4R,6S) stereoisomer.

Synthesis and biological evaluation of potential 5-HT7 receptor PET radiotracers

Brain serotonin 7 receptor (5-HT7) is involved in several mood disorders and drug candidates targeting this subtype are currently in development. Positron emission tomography (PET) is a molecular imaging modality offering great promise for accelerating the process from preclinical discovery to clinical phases. As no PET radiopharmaceutical has yet been used successfully to study the 5-HT7 receptor in vivo, our objective is to develop the first 5-HT7 fluorine-18 labeled radiotracer. Four structural analogs of SB269970, a specific 5-HT7 receptor antagonist, divided in FP3 series and FPMP series were synthesized. Their antagonist effects were investigated by cellular functional assay. Nitro-precursors of these analogs were radiolabeled via a [18F-]nucleophilic substitution and in vitro autoradiographies were performed in rat brain. Chemical and radiochemical purities of fluorine radiotracers were >99% with specific activities in 40-129 GBq/μmole range. The four derivates presented antagonism potencies toward 5-HT7 receptors (pKB) between 7.8 and 8.8. The four PET radiotracers had suitable characteristic for 5-HT7 receptor probing in vitro even if the FP3 series seemed to be more specific for this receptor. These results encourage us to pursue in vivo studies.

SUBSTITUTED BENZHYDRYLETHERS

Disclosed herein are substituted benzhydrylethers of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of their use thereof.

Endomorphin-1 analogues containing β-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance

In this paper we describe the synthesis and affinity toward the μ-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind μ -opioid receptors depends on the β-amino acid, and in particular 4, which contains β-L-Pro, has a KI, in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as the μ-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as μ-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential μ-opioid receptor agonists.

Oligomers of β2- and of β3-homoproline: What are the secondary structures of β-peptides lacking H-bonds?

To study the role of H-bonds in stabilizing β-peptidic secondary structures, we have synthesized β-oligopeptides (up to the octadecamer 12) consisting of β2- and β3-homoproline, i.e., β-peptides lacking amide protons. The enantiomer purity of the building block β2-homoproline (nipecotic acid, 4) was determined by HPLC analysis of the N-(2,4- dinitrophenyl) derivative 5 on a Chiralcel-OD column (cf. Fig. 2). The CD spectra of the all-(S)-β2- and all-(S)-β3-HPro-containing, β-peptides display novel and intensive CD patterns which may be indicative of a secondary structure (cf. Fig. 3). It is noteworthy that a distinct CD pattern was observed with the β3-HPro derivatives containing as few as three residues (7a). The crystal structure of a N-deprotected β3-HPro-tripeptide 7c is presented (cf. Figs. 4 and 5), and a model for the structure of β- peptides consisting of β3-HPro is discussed (cf. Figs. 6 and 7).