6404-31-5

Basic information

• Product Name: N-Benzyloxycarbonyl-D-proline
• Synonyms: Cbz-D-Pro;PROLINA-Z-D;(R)-Z-pyrrolidine-2-carboxylic acid;Z-D-proline≥ 98% (HPLC);1,2-PYRROLIDINEDICARBOXYLIC ACID, 1-(PHENYLMETHYL)ESTER, (2R)-;1,2-PYRROLIDINEDICARBOXYLIC ACID, 1-(PHENYLMETHYL) ESTER, (R)-;1-[(BENZYLOXY)CARBONYL]PYRROLIDINE-2-CARBOXYLIC ACID;BENZYLOXYCARBONYL-D-PROLINE
• CAS NO: 6404-31-5
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.26
• EINECS: 229-021-5
• Product Categories: Proline [Pro, P];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Cbz-Amino acid series;Amino Acid Derivatives;Peptide Synthesis;Proline
• Mol File: 6404-31-5.mol

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 432.3 °C at 760 mmHg
• Flash Point: 215.3 °C
• Appearance: White/Crystalline Powder or Powder
• Density: 1.309 g/cm³
• Vapor Pressure: 3.06E-08mmHg at 25°C
• Refractive Index: 40 ° (C=2, EtOH)
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 3.99±0.20(Predicted)
• BRN: 485188
• CAS DataBase Reference: N-Benzyloxycarbonyl-D-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyloxycarbonyl-D-proline(6404-31-5)
• EPA Substance Registry System: N-Benzyloxycarbonyl-D-proline(6404-31-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6404-31-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyloxycarbonyl-D-proline is used as a key intermediate in the synthesis of histone deacetylase inhibitors, such as trichostatin A and trapoxin B analogs. These inhibitors play a crucial role in regulating gene expression and have potential applications in the treatment of various diseases, including cancer.
Used in Biochemistry Research:
N-Benzyloxycarbonyl-D-proline is also used in the preparation of potent and selective nonpeptide inhibitors of caspases 3 and 7. Caspases are enzymes involved in the regulation of apoptosis, and their inhibition can provide valuable insights into the mechanisms of cell death and potential therapeutic targets for various diseases.

InChI:InChI=1/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/p-1/t11-/m1/s1

Upstream product

• 99464-81-0 benzyl (1-chloroethyl) carbonate 
• 344-25-2 D-Prolin 
• 501-53-1 benzyl chloroformate 
• 50463-82-6 (2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate 
• 609-36-9 rac-Pro-OH 
• 1148-11-4 N-carbobenzyloxyproline 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 200499-54-3 (R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde 
• 200499-57-6 (2R,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine 
• 100-51-6 benzyl alcohol 
• 147-85-3 L-proline 
• 75819-24-8 3-benzyloxycarbonyl-2-oxazolone 
• 147-85-3 (S)-proline 
• 640-68-6 D-Val-OH 

Downstream Products

• 107164-48-7 N-carbobenzyloxy-D-prolyl-L-proline p-nitrophenyl ester 
• 80630-78-0 CBZ-(R)-Pro-PPM 
• 7672-21-1 (Z)-D-Pro-Leu-Gly-NH₂ 
• 82113-13-1 N-(benzyloxycarbonyl)-D-prolyl-L-alanyl-α-aminoisobutyryl-L-phenylalanine 2,2,2-trichloroethyl ester 
• 140834-97-5 Z-D-Pro-Gln-Gln-OBzl 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 
• 62937-47-7 (2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 344-25-2 D-Prolin 
• 2766-31-6 ethyl {[(2S)-1-(benzyloxycarbonyl)pyrrolidin-2-yl]ccarbonylamino}acetate 
• 878232-24-7 1-benzyloxycarbonyl-N-[3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropyl]-D-prolineamide 
• 878232-02-1 1-benzyloxycarbonyl-N-[3-spiro(2,3-dihydro-1H-indene-1,4'-piperidine)-1-ylpropyl]-D-prolineamide 
• 910050-04-3 (R)-2-(4-benzyl-piperidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 187993-58-4 (2R)-1-benzyloxycarbonyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine 

Relevant articles and documents

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.

Macrocyclic MCL-1 inhibitors and methods of use

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

3-(trimethylsilyl) pyrrolidine-2-carboxylic acid, its intermediate, preparation and application thereof

The invention relates to 3-(trimethylsilyl) pyrrolidine-2-carboxylic acids, its intermediates , preparation and application thereof, the structural formula of the described 3-(trimethylsilyl) pyrrolidine-2-carboxylic acid is (the structural formula of the described 3-(trimethylsilyl) pyrrolidine-2-carboxylic acid is shown in the description). The preparation method uses chiral proline as raw material, and carries out C-H bond activation reaction with silanization reagent after protective group and adjuvant are introduced, then an intermediate is obtained after removing protective group; the intermediate can remove auxiliary groups under the acid action and the described 3-(trimethylsilyl) pyrrolidine-2-carboxylic acid can be obtained. 3-(trimethylsilyl) pyrrolidine-2-carboxylic acids are used in asymmetric catalytic reactions. The reaction condition of the 3-(trimethylsilyl) pyrrolidine-2-carboxylic acid is mild, with high chemical yield, which provides a new way for the synthesis of the silicon-containing structural analogue, and the prepared (2R, 3R)-3-(trimethylsilyl) pyrrolidine-2-carboxylic acid, (2S, 3S)-3-(trimethylsilyl) pyrrolidine-2-carboxylic acid can be used as chiral catalyst for asymmetric reaction, and has good application prospect.

HUMAN PLASMA KALLIKREIN INHIBITORS

Disclosed are compounds of formula I, and pharmaceutically acceptable salts thereof. The compounds are inhibitors of plasma kallikrein. Also provided are pharmaceutical compositions comprising at least one compound of the invention, and methods involving use of the compounds and compositions of the invention in the treatment and prevention of diseases and conditions characterized by unwanted plasma kallikrein activity.

BIPHENYL COMPOUNDS AND USES THEREOF

The present invention relates to biphenyl compounds and uses thereof in medicine. Specifically, the present invention relates to a compound of Formula (I), or a stereoisomer, a geometric isomer, a tautomer, a mesomer, a racemate, an enantiomer, a diastereoisomer, an N-oxide, a hydrate, a solvate, a metabolite, a hydrolysate, a pharmaceutically acceptable salt or a prodrug thereof. The compound disclosed herein is used as a therapeutic agent particularly a GPR40 agonist for treating diabetes and metabolic disease in a patient.

Synthesis of (-)-(S, S)-clemastine by invertive N → C aryl migration in a lithiated carbamate

The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of α-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement.

Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)

A series of platinum(II) complexes were synthesised based on the enantiomerically pure amino acid proline. Novel synthetic pathways were developed, adapted from standard peptide chemistry, to produce the 2-aminomethylpyrrolidine (pyrr) ligand and its derivatives with differing arrangements of methyl substituents at the exocyclic amine sites. The crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N,N-dimethyl-2(R)-aminomethylpyrrolidine) is reported and the five-membered ligand ring has been shown to be in an envelope conformation. Cytotoxicity studies were carried out on the ovarian cancer A2780 tumour cell line and its cisplatin-resistant variant, A2780cisR. Remarkably good activity was seen for several of the drugs when compared to cisplatin despite the addition of substantial steric bulk to the amine groups, and there was a lack of cross-resistance with cisplatin seen for some compounds.

Large nonlinear effect observed in the enantiomeric excess of proline in solution and that in the solid state

(Chemical Equation Presented) A clue to the origin of chirality? A solution of proline with high enantiomeric excess (85-99% ee) was obtained from solid proline of only 10% ee through novel dissolution and crystallization processes (see scheme). This observation may be an explanation for the origin of chirality on Earth.

Role of secondary structure in the asymmetric acylation reaction catalyzed by peptides based on chiral Cα-tetrasubstituted α-amino acids

In a recent series of papers, Miller and co-workers were able to show that His(π-Me)-based, terminally protected peptides are potent catalysts of the asymmetric acyl transfer reaction, useful for the kinetic resolution of alcohols. In a structure-supporting solvent, one of the most active compounds, an Aib-containing tetrapeptide, is folded in a doubly intramolecularly H-bonded β-hairpin motif incorporating a type-II′ β-turn conformation. In this work, we have expanded the study of the Miller tetrapeptide by examining a set of analogues and shorter sequences (dipeptide amides), characterized by chiral Cα-tetrasubstituted α-amino acids of diverging bulkiness and optical configuration. Peptide synthesis in solution, conformational analysis by FT-IR absorption and 1H NMR techniques, and screening of catalytic activity as well have been performed. Our results confirm the close relationship between the β-hairpin 3D-structure and the catalytic activity of the peptides. A tetrapeptide analogue slightly more selective than the Miller compound has been found. However, the terminally protected, industrially more appealing, dipeptide amides are poorly effective.

Enantioselective Enzymatic Cleavage of N-Benzyloxycarbonyl Groups

A new enzymatic process for the enantioselective cleavage of N-benzyloxycarbonyl (Cbz) groups from protected amino acids and related compounds has been developed. The Cbz-deprotecting enzyme was isolated from cell extracts of Sphingomonas paucimobilis SC 16113 and purified to homogeneity. The purified protein has a molecular weight of 155,000 daltons and a subunit size of 44,000 daltons.