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

Downstream Products

• 702679-96-7 Ac-[γAmp(N^α-Ac)]-NH2 
• 132622-66-3 cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline 
• 936479-72-0 (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1386458-54-3 (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 
• 1207593-27-8 C₃₃H₃₃N₃O₄S 
• 1207593-29-0 C₂HF₃O₂*C₂₈H₂₅N₃O₂S 
• 1207593-30-3 C₃₉H₄₄N₄O₅S 
• 1207593-32-5 C₂HF₃O₂*C₃₄H₃₆N₄O₃S 
• 1207593-33-6 C₄₃H₅₁N₅O₆S 
• 1207593-34-7 C₂₈H₄₁N₅O₄S 

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.

Superior HIV-1 TAR Binders with Conformationally Constrained R52 Arginine Mimics in the Tat(48–57) Peptide

We report a 100-fold increase in binding affinity of the Tat(48–57) peptide to HIV-1 transcriptional activator-responsive element (TAR) RNA by replacing Arg52, an essential and critical residue for Tat's specific binding, with (2S,4S)-4-guanidinoproline. The resulting αTat1M peptide is a far superior binder than γTat1M, a peptide containing another conformationally constrained arginine mimic, (2S,4S)-4-amino-N-(3-guanidinopropyl)proline, or even the control Tat peptide (CtrlTat) itself. Our observations are supported by circular dichroism (CD), isothermal titration calorimetry (ITC), gel electrophoresis and UV spectroscopy studies. Molecular dynamics simulations suggest increased interactions between the more compact αTat1M and TAR RNA, relative to CtrlTat. The CD signature of the RNA itself remains largely unchanged upon binding of the peptides. The Tat mimetics further have better cell uptake properties than the control Tat peptide, thus increasing their potential application as specific TAR-binding molecules.

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.