33996-33-7 Usage
Chemical Properties
White powder
Originator
Jonctum,Merrell,France,1970
Uses
trans-1-Acetyl-4-hydroxy-L-proline can be used:In the stereospecific synthesis of 4-fluoroglutamic acid.To synthesize molecular targets for von Hippel-Lindau (VHL) E3 ubiquitin ligase.As a precursor to synthesize pseudopoly(amino acids) such as poly(trans-4-hydroxy-4-acyl-L-proline ester) and a biodegradable polymer, poly(lactic acid-glycolic acid-4-hydroxyproline).
Manufacturing Process
16.7 g (0.127 mol) of L-hydroxyproline are dissolved in 400 ml of pure boiling acetic acid. With vigorous boiling and agitation, a mixture of 13.7 ml (0.154 mol) of rectified acetic anhydride and 250 ml of pure acetic acid is added during 25 minutes. Without discontinuing the stirring, contents of the flask are cooled by simply causing fresh air to circulate externally round the flask until the temperature of the mixture is reduced to about 35°C. The acetic acid is removed by using a rotary evaporator without exceeding 35°C under a vacuum of about 15 mm Hg. After one hour, 20 ml of anhydrous toluene are added, then 10 ml of anhydrous acetone; the mixture is homogenized and concentrated again as above during 30 minutes. Then 25 ml of acetone are added again, and subsequently 20 ml of toluene, the product being concentrated again; gradually the solution is converted into an amber-colored crystallized paste. Finally, 30 ml of acetone are added to the residue, and stirring is carried out until the oily fraction surrounding the crystals is dissolved. The product is then cooled in an ice chamber, centrifuged, washed with anhydrous acetone and eventually dried, After recrystallization from acetone, crystals are obtained, melting point 132°C.
Therapeutic Function
Antirheumatic
Flammability and Explosibility
Notclassified
Check Digit Verification of cas no
The CAS Registry Mumber 33996-33-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,9,9 and 6 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 33996-33:
(7*3)+(6*3)+(5*9)+(4*9)+(3*6)+(2*3)+(1*3)=147
147 % 10 = 7
So 33996-33-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO4/c1-4(9)8-3-5(10)2-6(8)7(11)12/h5-6,10H,2-3H2,1H3,(H,11,12)/p-1/t5-,6+/m1/s1
33996-33-7Relevant articles and documents
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Prange et al.
, p. 104,108 (1974)
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Energetic contribution to both acidity and conformational stability in peptide models
Kubyshkin, Vladimir,Durkin, Patrick,Budisa, Nediljko
supporting information, p. 5209 - 5220 (2016/07/06)
The acidity of N-acyl amino acids is dependent upon the rotameric state of the amide bond. In this work we systematically investigated the acidity difference of the rotamers (ΔpKa) in the frames of various acetylated amino acids. Our results indicated a mutual interaction of two carbonyl groups of an attractive type. We observed conservative ΔpKas for acyclic amino acids (2.2-3.0 kJ mol-1), whereas in the case of alicyclic amino acids, the experimental values revealed a strong dependency on the structural context (1.5-4.4 kJ mol-1). In homologous amino acids (α-, β-, γ-, etc.), the strength of the attraction decays in an exponential fashion. Furthermore, the interaction can accumulate through a chain of amide bonds in a cascade fashion, as demonstrated by an Ac-Pro-Pro dipeptide. As a result, we demonstrate that ΔpKa is an experimental parameter to estimate increments in the carbonyl-carbonyl alignment, as determined by the amino acid or peptidyl context. This parameter is also important in understanding the roles of amino acids in both protein folding and translation in biological systems as well as their evolutionary appearance in the genetic code.
