174148-03-9

Basic information

• Product Name: N-Boc-cis-4-Fmoc-Amino-L-proline
• Synonyms: (±) cis-4-(N-FMoc-AMino) N-Boc nipecotic acid;(4S)-4-(FMoc-aMino)-1-Boc-L-proline;N-Boc-cis-4-N-Fmoc-amino-L-proline 97%;N-BOC-CIS-4-N-FMOC-AMINO-L-PROLINE 97;N-Boc-cis-4-FMOC-Amino-L-Proline;1,2-Pyrrolidinedicarboxylicacid,4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-,1-(1,1-dimethylethyl)ester,(2S,4S)-(9CI);(2S,4S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester;(2S,4S)-Pyrrolidine-2-carboxylic acid, N1-BOC 4-FMOC protected
• CAS NO: 174148-03-9
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.5
• Product Categories: FMOC
• Mol File: 174148-03-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 150-154 °C(lit.)
• Boiling Point: 650.2 °C at 760 mmHg
• Flash Point: 347.029 °C
• Appearance: White to off-white crystalline powder
• Density: 1.33
• Refractive Index: 1.627
• Storage Temp.: Store at 0-5°C
• PKA: 3.81±0.40(Predicted)
• CAS DataBase Reference: N-Boc-cis-4-Fmoc-Amino-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-cis-4-Fmoc-Amino-L-proline(174148-03-9)
• EPA Substance Registry System: N-Boc-cis-4-Fmoc-Amino-L-proline(174148-03-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 174148-03-9(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

also available as trans isomer, see 1-00972

InChI:InChI=1/C25H28N2O6/c1-25(2,3)33-24(31)27-13-15(12-21(27)22(28)29)26-23(30)32-14-20-18-10-6-4-8-16(18)17-9-5-7-11-19(17)20/h4-11,15,20-21H,12-14H2,1-3H3,(H,26,30)(H,28,29)/t15-,21-/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 121148-01-4 (2S,4S)-4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 84520-68-3 N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 132622-66-3 cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline 

Relevant articles and documents

Characterization of Specific N-α-Acetyltransferase 50 (Naa50) Inhibitors Identified Using a DNA Encoded Library

Two novel compounds were identified as Naa50 binders/inhibitors using DNA-encoded technology screening. Biophysical and biochemical data as well as cocrystal structures were obtained for both compounds (3a and 4a) to understand their mechanism of action. These data were also used to rationalize the binding affinity differences observed between the two compounds and a MLGP peptide-containing substrate. Cellular target engagement experiments further confirm the Naa50 binding of 4a and demonstrate its selectivity toward related enzymes (Naa10 and Naa60). Additional analogs of inhibitor 4a were also evaluated to study the binding mode observed in the cocrystal structures.

Antibacterial and anti-TB tat-peptidomimetics with improved efficacy and half-life

Non-natural antimicrobial peptides are ideal as next-generation antibiotics because of their ability to circumvent the problems of drug resistance and in vivo instability. We report novel all-α- and α,γ-mixed Tat peptide analogues as potential antibacterial and anti-TB agents. These peptides have broad spectrum antibacterial activities against Gram-positive (MICs 0.61 ± 0.03 to 1.35 ± 0.21 μM with the peptide γTatM4) and Gram-negative (MICs 0.71 ± 0.005 to 1.26 ± 0.02 μM with γTatM4) bacteria and are also effective against active and dormant forms of Mycobacterium tuberculosis, including strains that are resistant to rifampicin and isoniazid. The introduction of the non-natural amino acids of the study in the Tat peptide analogues results in increased resistance to degradation by proteolysis, significantly increasing their half-life. The peptides appear to inhibit bacteria by a membrane disruption mechanism, and have only a low cytotoxic effect on mammalian cells.

ANTIVIRAL COMPOUNDS

The invention is related to phosphorus substituted anti-viral inhibitory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.