440361-71-7

Basic information

• Product Name: (R)-PYRROLIDINE-2-CARBALDEHYDE
• Synonyms: (R)-PYRROLIDINE-2-CARBALDEHYDE
• CAS NO: 440361-71-7
• Molecular Formula: C5H9NO
• Molecular Weight: 99.13
• Mol File: 440361-71-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-PYRROLIDINE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-PYRROLIDINE-2-CARBALDEHYDE(440361-71-7)
• EPA Substance Registry System: (R)-PYRROLIDINE-2-CARBALDEHYDE(440361-71-7)

Safety Data

• Hazardous Substances Data: 440361-71-7(Hazardous Substances Data)

Upstream product

• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 69610-41-9 Boc-L-Pro-H 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 147-85-3 L-proline 
• 17004-36-3 [5']adenylic acid L-proline anhydride 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 73365-02-3 tert-butoxycarbonyl-D-prolinal 

Relevant articles and documents

Biosynthesis, Mechanism of Action, and Inhibition of the Enterotoxin Tilimycin Produced by the Opportunistic Pathogen Klebsiella oxytoca

Tilimycin is an enterotoxin produced by the opportunistic pathogen Klebsiella oxytoca that causes antibiotic-associated hemorrhagic colitis (AAHC). This pyrrolobenzodiazepine (PBD) natural product is synthesized by a bimodular nonribosomal peptide synthetase (NRPS) pathway composed of three proteins: NpsA, ThdA, and NpsB. We describe the functional and structural characterization of the fully reconstituted NRPS system and report the steady-state kinetic analysis of all natural substrates and cofactors as well as the structural characterization of both NpsA and ThdA. The mechanism of action of tilimycin was confirmed using DNA adductomics techniques through the detection of putative N-2 guanine alkylation after tilimycin exposure to eukaryotic cells, providing the first structural characterization of a PBD-DNA adduct formed in cells. Finally, we report the rational design of small-molecule inhibitors that block tilimycin biosynthesis in whole cell K. oxytoca (IC50 = 29 ± 4 μM) through the inhibition of NpsA (KD = 29 ± 4 nM).

Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form

Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.

Compound (E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride and synthetic method

The invention discloses a compound (E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride and a synthetic method. The compound is structurally as shown in a formula (I). The synthetic method of the compound comprises the following steps: using BOC-L-prolinol (or BOC-D-prolinol) as an initial material, and by oxidization, forming aldehyde; removing a BOC protective agent; then reacting with haloalkane; then by a Wittig reaction, synthesizing (S,E)-3-(1-methylpyrrolidine-2-yl)-ethyl acrylate; after hydrolysis, salifying to obtain (S,E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride [or (R,E)-3-(1-methylpyrrolidine-2-yl)-acrylic hydrochloride]. The compound, as a medical intermediate, can be used for preparing quinazoline or quinolines medicine derivatives. The formula is shown in the description.

Compounds which inhibit leukocyte adhesion mediated by VLA-4

Disclosed are compounds which bind VAL-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g.

Synthesis of dolastatin 10

A complicated but extremely important scheme of synthesis has been developed for synthesizing, dolaisoleuine, dolaproine, dolaphenine and dolavaline from readily available starting materials such as Z-(S,S)isoleucine, S-phenylalaline, S-phenylalaninol, S-prolinol, S-mandelate, and S-valine. The requisite amino acids have been combined using several peptide coupling procedures to create pharmaceutically pure dolastatin 10.