58919-61-2 Usage
Uses
Coprine is a poisonous toxin that is found in mushrooms resulting in coprinus syndrome.
Definition
ChEBI: A non-proteinogenic L-alpha-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Cop
inus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect').
Check Digit Verification of cas no
The CAS Registry Mumber 58919-61-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,9,1 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 58919-61:
(7*5)+(6*8)+(5*9)+(4*1)+(3*9)+(2*6)+(1*1)=172
172 % 10 = 2
So 58919-61-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1
58919-61-2Relevant academic research and scientific papers
A New Synthesis of Coprine and O-Ethylcoprine
Kienzler, Thomas,Strazewski, Peter,Tamm, Christoph
, p. 1078 - 1084 (2007/10/02)
Coprine (1), a toxine of the mushroom Coprinus atramentarius, was synthesized starting from the 2-amino- and 1-carboxy-protected L-glutamic acids 4 and 12.Compound 4 was first decarboxylated by radical chain reaction to bromide 5 which underwent ring closure to cyclopropanecarboxylate 6 on treatment with NaH (Scheme 1).Subsequent oxidative electrolysis of 7 to form tert-butyl N-(1-ethoxycyclopropyl)carbamate (8) and acidic hydrolysis yielded the 1-aminocyclopropanol hydrochloride (9).Selective cleavage of the amino-protecting group of 8(-> 10 or 11), coupling of the corresponding amine 13 with L-glutamic acid 12, and acidic hydrolysis of the resulting L-glutamine derivative 17 yielded O-ethylcoprine (3) and coprine (1).
