74844-91-0

Basic information

• Product Name: N-Boc-trans-4-Hydroxy-L-proline methyl ester
• Synonyms: N-T-BOC-TRANS-4-HYDROXY-L-PROLINE METHYL ESTER;N-(TERT-BUTOXYCARBONYL)-TRANS-HYDROXYL-L-PROLINE METHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-L-HYDROXYPROLINE METHYL ESTER;N-BOC-TRANS-4-HYDROXYL-L-PROLINE METHYL ESTER;N-BOC-TRANS-4-HYDROXY-L-PROLINE METHYL ESTER;N-BOC-4-HYDROXY-L-PROLINE METHYL ESTER;N-BOC-L-TRANS-4-HYDROXY-PROLINE METHYL ESTER;(2R,4R)-4-HYDROXY-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER
• CAS NO: 74844-91-0
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.27
• EINECS: 1592732-453-0
• Product Categories: Amino Acids and Derivatives;Hydroxyproline [Hyp];Unusual Amino Acids;Amino Acids 13C, 2H, 15N;Boc-Amino acid series;Amino Acids & Derivatives;Heterocycles;Peptide Synthesis;Proline Derivatives;Unnatural Amino Acid Derivatives
• Mol File: 74844-91-0.mol
• Article Data: 185

Chemical Properties

• Melting Point: 92-96 °C(lit.)
• Boiling Point: 132°C/0.05mmHg(lit.)
• Flash Point: 156.55 °C
• Appearance: White to light beige/Crystalline Powder
• Density: 1.217 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform, dichloromethane and ethyl acetate.
• PKA: 14.27±0.40(Predicted)
• CAS DataBase Reference: N-Boc-trans-4-Hydroxy-L-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-trans-4-Hydroxy-L-proline methyl ester(74844-91-0)
• EPA Substance Registry System: N-Boc-trans-4-Hydroxy-L-proline methyl ester(74844-91-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 74844-91-0(Hazardous Substances Data)

Usage

Description

N-Boc-trans-4-Hydroxy-L-proline methyl ester is a chemical compound with the molecular formula C10H19NO4. It is a clear, colorless oil and is a derivative of L-proline, an essential amino acid. N-Boc-trans-4-Hydroxy-L-proline methyl ester features a hydroxyl group, an ester group, and a tert-butyloxycarbonyl (Boc) protecting group, which makes it a versatile building block in organic synthesis and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
N-Boc-trans-4-Hydroxy-L-proline methyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential applications in treating different diseases.
Used in Organic Synthesis:
N-Boc-trans-4-Hydroxy-L-proline methyl ester is used as a building block in organic synthesis for the creation of complex molecules. Its functional groups can be selectively modified to produce a wide range of compounds with diverse properties and applications.
Used in Inhibitor Development:
N-Boc-trans-4-Hydroxy-L-proline methyl ester is used as a potential inhibitor of inducible nitric oxide synthase (iNOS), an enzyme involved in various physiological and pathological processes. Inhibiting iNOS can have therapeutic benefits in conditions such as inflammation, pain, and neurodegenerative diseases.
Used in Synthesis of (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester:
N-Boc-trans-4-Hydroxy-L-proline methyl ester is used as a key component in the synthesis of (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester, a compound with potential applications in the pharmaceutical industry.
Used in Synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) Analogues:
N-Boc-trans-4-Hydroxy-L-proline methyl ester is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues, which are based on the replacement of the Met residue by a 4-amino-proline scaffold. These analogues have potential applications in the development of new drugs targeting various biological processes.
Chemical Properties:
N-Boc-trans-4-Hydroxy-L-proline methyl ester is a clear, colorless oil with the molecular formula C10H19NO4. Its chemical properties include the presence of a hydroxyl group, an ester group, and a Boc protecting group, which contribute to its reactivity and versatility in chemical synthesis and pharmaceutical applications.

InChI:InChI=1/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1

Upstream product

• 84520-68-3 N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester 
• 67-56-1 methanol 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 77-78-1 dimethyl sulfate 
• 34619-03-9 tert-butyldicarbonate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 3398-22-9 trans-4-hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 32968-78-8 (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid hydrochloride 
• 1063998-64-0 (2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride 
• 104241-31-8 (2S,4S)-2-(tert-butoxycarbonyl)amino-3,4-epoxypentanoic acid methyl ester 
• 106391-74-6 (2S,4R)-2-(tert-butoxycarbonyl)amino-4-formyl-γ-butyrolactone 

Downstream Products

• 629616-63-3 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-{[(4-nitrophenyl)sulfonyl]oxy}-2,3,4,5-tetrahydro-1H-pyrrole-1,2-dicarboxylate 
• 848475-20-7 (4R)-4-[(4'-bromobenzyl)oxy]-N-Boc-L-proline methyl ester 
• 259214-70-5 (2S,4R)-4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 808154-91-8 [2-Amino-4-(5-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentyloxy)-5-methoxy-phenyl]-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-84-9 [4-(5-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentyloxy)-5-methoxy-2-nitro-phenyl]-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-82-7 [4-(4-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-butoxy)-5-methoxy-2-nitro-phenyl]-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-80-5 [4-(3-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-propoxy)-5-methoxy-2-nitro-phenyl]-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-89-4 [2-Amino-4-(4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butoxy)-5-methoxy-phenyl]-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-87-2 [2-Amino-4-(3-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-propoxy)-5-methoxy-phenyl]-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-72-5 (4-Benzyloxy-5-methoxy-2-nitro-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-68-9 methyl (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-difluoromethylidenepyrrolidine-2-carboxylate 
• 808154-74-7 (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal 
• 808154-77-0 (2-Amino-4-hydroxy-5-methoxy-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 
• 808154-70-3 (S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-difluoromethylene-pyrrolidine-2-carbaldehyde 

Relevant articles and documents

Construction of Challenging Proline-Proline Junctions via Diselenide-Selenoester Ligation Chemistry

Polyproline sequences are highly abundant in prokaryotic and eukaryotic proteins, where they serve as key components of secondary structure. To date, construction of the proline-proline motif has not been possible owing to steric congestion at the ligatio

C3′-endo-puckered pyrrolidine containing PNA has favorable geometry for RNA binding: Novel ethano locked PNA (ethano-PNA)

A novel peptide nucleic acid (PNA) analogue is designed with a constraint in the aminoethyl segment of the aegPNA backbone so that the dihedral angle β is restricted within 60-80, compatible to form PNA:RNA duplexes. The designed monomer is further functionalized with positively charged amino-/guanidino-groups. The appropriately protected monomers were synthesized and incorporated into aegPNA oligomers at predetermined positions and their binding abilities with cDNA and RNA were investigated. A single incorporation of the modified PNA monomer into a 12-mer PNA sequence resulted in stronger binding with complementary RNA over cDNA. No significant changes in the CD signatures of the derived duplexes of modified PNA with complementary RNA were observed.

Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices

The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.

Synthesis process of N-BOC-cis-4-hydroxyproline methyl ester

The invention discloses a synthesis process of N-BOC-cis-4-hydroxyproline methyl ester. The synthesis process comprises the following steps: (1) adding raw materials including dichloromethane, 4-hydroxy-L-proline and DMAP into a 2 L reaction flask, stirring, slowly dropwise adding BOC anhydride into the reaction liquid, after dropwise adding, sampling, carrying out TLC, completely reacting the rawmaterials, adding water into the reaction liquid after treatment, stirring at a temperature of 20-30 DEG C, separating the liquid, drying an organic phase by using anhydrous sodium sulfate, and concentrating under reduced pressure to obtain a white solid product; and (2) taking the obtained product, adding tetrahydrofuran and DCC into a 5 L reaction flask, stirring at 20-30 DEG C to react for 1 hour, dropwise adding methanol into the reaction solution, keeping the temperature after dropwise adding, sampling, carrying out TLC until the reaction is complete, filtering the reaction solution, collecting the filtrate, concentrating under reduced pressure until no liquid flows out to obtain a white solid crude product, heating, collecting the filtrate, collecting a filter cake, and drying the filter cake to obtain a white solid. According to the invention, the product is prepared with high quality and high yield.

Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates

Alpha-amanitin, an extremely toxic bicyclic octapeptide extracted from the death-cap mushroom, Amanita phalloides, is a highly selective allosteric inhibitor of RNA polymerase II. Following on growing interest in using this toxin as a payload in antibody-drug conjugates, herein we report the synthesis and biochemical evaluation of several new derivatives of this toxin to probe the role of the trans-hydroxyproline (Hyp), which is known to be critical for toxicity. This structure activity relationship (SAR) study represents the first of its kind to use various Hyp-analogs to alter the conformational and H-bonding properties of Hyp in amanitin.