15401-08-8

Basic information

• Product Name: BOC-PRO-PRO-OH
• Synonyms: N-T-BOC-PRO-PRO;BOC-PRO-PRO-OH;boc-pro-pro;N-(tert-butoxycarbonyl)-Pro-Pro;(S)-1-((S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid;(tert-Butoxycarbonyl)prolylproline;Boc-L-Prolyl-L-proline;N-(tert-Butoxycarbonyl)prolylproline
• CAS NO: 15401-08-8
• Molecular Formula: C₁₅H₂₄N₂O₅
• Molecular Weight: 312.36
• Product Categories: Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 15401-08-8.mol

Chemical Properties

• Melting Point: 185-187℃ (ethyl acetate hexane )
• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: BOC-PRO-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-PRO-PRO-OH(15401-08-8)
• EPA Substance Registry System: BOC-PRO-PRO-OH(15401-08-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 15401-08-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-PRO-PRO-OH is used as a building block in peptide synthesis for the development of peptide-based drugs. Its role is crucial in creating specific peptide sequences that can be used to target various medical conditions, taking advantage of the compound's ability to form stable and functional peptide chains.
Used in Biochemical Research:
In the field of biochemistry, BOC-PRO-PRO-OH serves as a valuable tool for studying the structure and function of proteins. Its use in peptide synthesis allows researchers to create and manipulate specific protein sequences, facilitating a deeper understanding of protein behavior and interactions within biological systems.
Used in Peptide Synthesis:
BOC-PRO-PRO-OH is used as a precursor in the synthesis of longer peptide chains. The presence of the BOC protecting group ensures that the proline molecules can be selectively incorporated into growing peptide sequences without unwanted side reactions, thus maintaining the integrity and specificity of the desired peptide product.
Overall, BOC-PRO-PRO-OH is an essential component in the advancement of peptide-based therapeutics and a versatile tool in biochemical research, underpinning its importance across various scientific and medical applications.

Upstream product

• 52386-41-1 N-tert-butoxycarbonyl-L-prolyl-L-proline methyl ester 
• 29776-70-3 N-(tert-butyloxycarbonyl)-prolyl-proline benzyl ester 
• 50903-52-1 (tert-butoxycarbonyl)-L-proline pentafluorophenol ester 
• 147-85-3 L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 32302-87-7 L?proline benzyl ester p?toluenesulfonate 
• 1280225-83-3 C₂₀H₃₀N₂O₆ 
• 24424-99-5 di-tert-butyl dicarbonate 
• 71989-31-6 Fmoc-Pro-OH 
• 41324-66-7 H-Pro-OBzl 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 125405-90-5 Boc-Pro-Pro-Gly-Ala-Gly-OBzl 
• 29776-72-5 Boc-Pro-Pro-Pro-OBzl 
• 87053-41-6 benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate 
• 67524-15-6 BOC-Pro-Pro-Gly-Gly-OBzl 
• 90296-96-1 (S)-2-{(S)-2-[({[((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-methyl)-carbamoyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 29776-73-6 Boc(L-Pro)4-Obn 
• 81094-39-5 Boc-Pro-Pro-Ala-Phe-OMe 
• 90315-56-3 (S)-2-((S)-2-{[((1S,2S)-1-Benzyloxycarbonyl-2-methyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 75666-42-1 Boc-Pro₂-Leu₃-OBzl 
• 87053-38-1 Boc-Pro-Pro-Phe-Ile-OBzl 
• 90296-93-8 (S)-2-[(S)-2-({[(S)-1-(Benzyloxycarbonylmethyl-carbamoyl)-2-phenyl-ethylcarbamoyl]-methyl}-carbamoyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 90282-73-8 N-(t-butoxycarbonyl)prolylprolylglycylisoleucylglycine benzyl ester 
• 90282-66-9 (S)-2-{(S)-2-[({[((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-carbamoyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 90297-00-0 (S)-2-{(S)-2-[(S)-1-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis of Prolylproline

Prolylproline has been synthesized by both classical peptide synthesis method utilizing tert-butoxycarbonyl or trifluoroacetyl protection of the NH group and carbodiimide-promoted peptide bond formation and by opening of the dioxopiperazine ring in octahydrodipyrrolo[1,2-a:1′,2′-d]pyrazine-5,10-dione obtained by thermolysis of proline methyl ester.

Permeation through phospholipid bilayers, skin-cell penetration, plasma stability, and CD spectra of α- And β-oligoproline derivatives

After a survey of the special role, which the amino acid proline plays in the chemistry of life, the cell-penetrating properties of polycationic proline-containing peptides are discussed, and the widely unknown discovery by the Giralt group (J. Am. Chem. Soc. 2002, 124, 8876) is acknowledged, according to which fluorescein-labeled tetradecaproline is slowly taken up by rat kidney cells (NRK-49F). Here, we describe details of our previously mentioned (Chem. Biodiversity 2004, 1, 1111) observation that a hexa-β3-Pro derivative penetrates fibroblast cells, and we present the results of an extensive investigation of oligo-L- and oligo-D-α-prolines, as well as of oligo-β2h- and oligo-β3h-prolines without and with fluorescence labels (1-8; Fig. 1). Permeation through protein-free phospholipid bilayers is detected with the nanoFAST biochip technology (Figs. 2-4). This methodology is applied for the first time for quantitative determination of translocation rates of cell-penetrating peptides (CPPs) across lipid bilayers. Cell penetration is observed with mouse (3T3) and human foreskin fibroblasts (HFF; Figs. 5 and 6-8, resp.). The stabilities of oligoprolines in heparin-stabilized human plasma increase with decreasing chain lengths (Figs. 9-11). Time- and solvent-dependent CD spectra of most of the oligoprolines (Figs. 13 and 14) show changes that may be interpreted as arising from aggregation, and broadening of the NMR signals with time confirms this assumption. Copyright

Synthesis of novel proline-based imidazolium ionic liquids

Abstract: A series of eight novel proline functionalized dipeptide imidazolium ionic liquids (DPILs), i.e. Boc-[Pro-Pro-EMIM], Boc-[Pro-Val-EMIM], Boc-[Pro-Ala-EMIM], Boc-[Pro-Phe-EMIM] containing [Cl] and [NTf2] anions were synthesized via a f

Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes

Abstract: Stereoselective Michael addition of enolizable carbonyl compounds to a furane-derived nitroalkene was catalyzed by di- and tripeptide organocatalysts. The most competent catalysts were tripeptides possessing Pro–Pro–Glu structure. With aldehydes

Proline-Rich Short Peptides with Photocatalytic Activity for the Nucleophilic Addition of Methanol to Phenylethylenes

Short proline-rich peptides were synthesized and modified with 1-(N,N-dimethylamino)pyrene by copper(I)-catalyzed cycloaddition. They perform photoredox catalysis of the nucleophilic addition of methanol to 1,1-diphenylethylene derivatives into products with Markovnikov orientation. The common additive triethylamine is avoided because forward and backward electron transfer is controlled by substrate binding. A free carboxylic function in the substrate allows more precise substrate binding and defines the electron transfer path better than the unspecific exciplex formation with the substrate bearing a carboxylic ester. A proline-type turn is an advantage for photoredox catalysis, but a proline-induced helix is not required. This is the first successful example for introducing secondarily structured peptides to photoredox catalysis.

Factors Affecting the Stabilization of Polyproline II Helices in a Hydrophobic Environment

Several parameters have a critical importance for the stabilization of either polyproline I (PPI) or polyproline II (PPII) helices in a hydrophobic environment. Among them, it was found out that the concentration is crucial as polyprolines at 3 mM concent

Compounds, compositions and use

A peptide comprising a unit of formula (I) and having a molecular weight of less than 2000 wherein each X is independently an organic group, e.g. a C1-6 alkyl or C1-6 alkenyl group, preferably —CH2—CH═CH2, or th

Hybrid bombesin analogues: Combining an agonist and an antagonist in defined distances for optimized tumor targeting

Radiolabeled hybrid ligands with defined distances between an agonist and an antagonist for the gastrin-releasing peptide receptor were found to have excellent tumor-targeting properties. Oligoprolines served as rigid scaffolds that allowed for tailoring distances of 10, 20, and 30 A between the recognition elements. In vitro and in vivo studies revealed that the hybrid ligand with a distance of 20 A between the recognition elements exhibits the highest yet observed tumor cell uptake and retention time in prostate cancer cells.

Asymmetric catalysis at the mesoscale: Gold nanoclusters embedded in chiral self-assembled monolayer as heterogeneous catalyst for asymmetric reactions

Research to develop highly versatile, chiral, heterogeneous catalysts for asymmetric organic transformations, without quenching the catalytic reactivity, has met with limited success. While chiral supramolecular structures, connected by weak bonds, are highly active for homogeneous asymmetric catalysis, their application in heterogeneous catalysis is rare. In this work, asymmetric catalyst was prepared by encapsulating metallic nanoclusters in chiral self-assembled monolayer (SAM), immobilized on mesoporous SiO2 support. Using olefin cyclopropanation as an example, it was demonstrated that by controlling the SAM properties, asymmetric reactions can be catalyzed by Au clusters embedded in chiral SAM. Up to 50% enantioselectivity with high diastereoselectivity were obtained while employing Au nanoclusters coated with SAM peptides as heterogeneous catalyst for the formation of cyclopropane- containing products. Spectroscopic measurements correlated the improved enantioselectivity with the formation of a hydrogen-bonding network in the chiral SAM. These results demonstrate the synergetic effect of the catalytically active metallic sites and the surrounding chiral SAM for the formation of a mesoscale enantioselective catalyst.

PEG prodrug of gambogic acid: Amino acid and dipeptide spacer effects

The clinical application of gambogic acid (GA), a natural component with promising antitumor activity, was limited due to its extremely poor aqueous solubility, rapid elimination in vivo, and wide biodistribution. To solve these problems, 30 poly(ethylene