273221-94-6

Basic information

• Product Name: N-BOC-TRANS-4-CYANO-L-PROLINE
• Synonyms: 4-Cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;trans-N-Boc-4-cyano-L-proline, 97%;(2S,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;(2S,4R)-4-Cyano-1,2-Pyrrolidinedicarboxylic acid 1-(tert-butyl) ester;(4R)-1-Boc-4-cyano-L-proline
• CAS NO: 273221-94-6
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 240.26
• Mol File: 273221-94-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 423.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.25
• Storage Temp.: 2-8°C
• PKA: 3.51±0.40(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: N-BOC-TRANS-4-CYANO-L-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-TRANS-4-CYANO-L-PROLINE(273221-94-6)
• EPA Substance Registry System: N-BOC-TRANS-4-CYANO-L-PROLINE(273221-94-6)

Safety Data

• Hazardous Substances Data: 273221-94-6(Hazardous Substances Data)

Usage

Uses

trans-N-Boc-4-cyano-L-proline is used as pharmaceutical intermediate.

Upstream product

• 194163-91-2 1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate 
• 121147-93-1 (2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 

Downstream Products

• 1399845-05-6 {(2S,5S)-2-[5-(4'-{2-[(2S,4R)-4-Cyano-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester 
• 1256389-40-8 ((S)-1-{(2S,4R)-2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester 
• 1399845-07-8 (3R,5S)-5-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-3-carbonitrile hydrochloride 
• 1256389-39-5 (2S,4R)-2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1222196-95-3 (2S,4R)-tert-butyl 4-cyano-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

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.