112240-59-2

Basic information

• Product Name: proclavaminic acid
• Synonyms: proclavaminic acid;(2S,3R)-2-(2-Oxo-1-azetidinyl)-3-hydroxy-5-aminopentanoic acid;(2S,3R)-2-(2-Oxoazetidine-1-yl)-3-hydroxy-5-aminovaleric acid;(2S,3R)-5-Amino-3-hydroxy-2-(2-oxoazetidin-1-yl)pentanoic acid
• CAS NO: 112240-59-2
• Molecular Formula: C8H14N2O4
• Molecular Weight: 202.21
• Mol File: 112240-59-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 526.3°Cat760mmHg
• Flash Point: 272.1°C
• Appearance: /
• Density: 1.445g/cm³
• Vapor Pressure: 2.82E-13mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: proclavaminic acid(CAS DataBase Reference)
• NIST Chemistry Reference: proclavaminic acid(112240-59-2)
• EPA Substance Registry System: proclavaminic acid(112240-59-2)

Safety Data

• Hazardous Substances Data: 112240-59-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H14N2O4/c9-3-1-5(11)7(8(13)14)10-4-2-6(10)12/h5,7,11H,1-4,9H2,(H,13,14)/t5-,7+/m1/s1

Upstream product

• 114342-07-3 5-azido-3-hydroxy-2-(2-oxoazetidin-1-yl)valeric acid 
• 114342-03-9 benzyl (2-oxo-azetidin-1-yl)acetate 
• 54643-14-0 ethyl (2-oxoazetidin-1-yl)acetate 
• 114342-05-1 ethyl 5-chloro-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 
• 114342-06-2 ethyl 5-azido-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 
• 130676-99-2 benzyl (3-bromopropionamido)acetate 
• 130712-20-8 (2S)-5-amino-2-(2'-oxazetidin-1'-yl)pentanoic acid 
• 130793-33-8 (2S,3R)-benzyl 5-azido-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 
• 116181-65-8 (2S,3R)-benzyl N⁵-benzyloxycarbonylamino-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 
• 130096-75-2 (S)-(2-benzyl-5R-isoxazolidin-5-yl)(2-oxaazetidin-1-yl)acetic acid benzyl ester 
• 865486-21-1 benzyl (4'S)-(4'-thiophenyl-2-'oxoazetidin-1'-yl) acetate 
• 865487-55-4 benzyl (2R,3R)-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(2-'oxoazetidin-1'-yl)pentanoate 
• 865487-27-0 benzyl (2R,3R,4'S)-5-(N-benzyloxycarbonyl)-amino-3-hydroxy-2-(4'-thiophenyl-2-'oxoazetidin-1'-yl)pentanoate 
• 73995-50-3 H-Orn(Z)-OBzl 

Downstream Products

• 130677-11-1 threo-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 
• 130677-11-1 (2S,3R)-4-nitrobenzyl 5-(4-bromophenylsulphonylamino)-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate 

Relevant articles and documents

A straightforward synthesis of proclavaminic acid, a biosynthetic precursor of clavulanic acid

A stereocontrolled synthesis of (2S,3R)-5-amino-3-hydroxy-2-(2-oxoazetin-1-yl) pentanoic acid, proclavaminic acid 3, has been achieved via the homochiral 4,5-disubstituted oxazolidin-2-one 4.

Product-substrate engineering by bacteria: Studies on clavaminate synthase, a trifunctional dioxygenase

Evidence is presented that clavaminate synthase (CS) catalyses three oxidative reactions in the clavulanic acid biosynthetic pathway. The first CS catalysed step (hydroxylation) is separated from the latter two (oxidative cyclisation and desaturation) by the action of a hydrolytic enzyme, proclavaminate amidinohydrolase, which modifies (or 'mutates') the sidechain of the product of the first reaction thereby converting it into a substrate for the second CS catalysed reaction.

Investigation of the Stereospecificity of Clavaminic Acid Synthase in the Desaturation of Dihydroclavaminic Acid to Clavaminic Acid

Incubations of (4R)- and (4S)--proclavaminic acid with clavaminic acid synthase resulted in the stereospecific removal of the deuterium and hydrogen respectively from C-4, in their conversions to clavaminic acid, suggesting an enzyme catalysed syn-