15537-71-0 Usage
Description
N-ACETYL-3-MERCAPTO-D-VALINE is an N-acetyl-D-amino acid, specifically where the amino acid is D-penicillamine. It is a derivative of D-penicillamine, which is an amino acid with a thiol (-SH) group. N-ACETYL-3-MERCAPTO-D-VALINE has unique properties due to the presence of the thiol group, which can form disulfide bonds and participate in various chemical reactions.
Uses
Used in Pharmaceutical Industry:
N-ACETYL-3-MERCAPTO-D-VALINE is used as a protected form of penicillamine for the pharmaceutical industry. The N-acetyl group serves as a protecting group, which can be removed under specific conditions to release the active D-penicillamine. This protection is crucial for stabilizing the compound during synthesis, formulation, or storage, preventing unwanted side reactions that could occur due to the reactivity of the thiol group.
Used in Antioxidant Applications:
N-ACETYL-3-MERCAPTO-D-VALINE can be used as an antioxidant in various industries, such as the food and pharmaceutical industries. The thiol group in the molecule can scavenge free radicals, protecting cells and tissues from oxidative damage. This property makes it a valuable additive for preserving the quality and shelf life of products.
Used in Chemical Synthesis:
In the field of chemical synthesis, N-ACETYL-3-MERCAPTO-D-VALINE can be used as a building block or intermediate for the synthesis of more complex molecules. The thiol group can participate in various reactions, such as thiol-disulfide exchange, Michael addition, and thiol-ene reactions, allowing for the creation of a diverse range of compounds with potential applications in various industries.
Used in Analytical Chemistry:
N-ACETYL-3-MERCAPTO-D-VALINE can be employed as a reagent or standard in analytical chemistry for the detection and quantification of specific compounds or ions. The thiol group can form stable complexes with certain metals or other molecules, which can be exploited for the development of analytical methods, such as colorimetric assays or chromatographic techniques.
Purification Methods
Both forms are recrystallised from hot H2O. A pure sample of the D-form is obtained after five recrystallisations. [Crooks in The Chemistry of Penicillin Clarke, Johnson and Robinson eds, Princeton University Press, 470 1949, Review: Chain et al. Antibiotics (Oxford University Press) 2 1949, Beilstein 4 III 1662.]
Check Digit Verification of cas no
The CAS Registry Mumber 15537-71-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,5,3 and 7 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 15537-71:
(7*1)+(6*5)+(5*5)+(4*3)+(3*7)+(2*7)+(1*1)=110
110 % 10 = 0
So 15537-71-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H13NO3S/c1-4(9)8-5(6(10)11)7(2,3)12/h5,12H,1-3H3,(H,8,9)(H,10,11)/t5-/m0/s1
15537-71-0Relevant articles and documents
15N NMR and electronic properties of S-nitrosothiols.
Wang,Hou,Zhang,Ksebati,Xian,Cheng,Wang
, p. 2897 - 2902 (1999)
Investigation of the 15N NMR of S-nitrosothiols showed that primary and tertiary RSNOs have distinct 15N chemical shifts around 730 and 790 ppm, respectively. Using 15N NMR technique, the equilibrium constant of NO transfer between SNAP and GSH was found to be 0.74. For primary RSNOs, linear relationships exist among 15N NMR chemical shifts, reduction potentials, and the pK(a)s of their parent thiols.
Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols
Wang, Kun,Wen, Zhong,Zhang, Wei,Xian, Ming,Cheng, Jin-Pei,Wang, Peng George
, p. 433 - 436 (2007/10/03)
Using UV-vis spectrometrical measurements, equilibrium constants for NO transfer between S-nitroso-N-acetyl-penicillamine (SNAP) and different thiols as well as kinetic data for NO transfer from S-nitroso bovine serum albumin (BSANO) to thiols have been obtained. NO transfer from SNAP to other primary/secondary thiols are thermodynamically favorable, whereas other S-nitrosothiols exhibit similar NO transfer potential. The obtained Gibbs free energy, enthalpy and entropy data indicated that NO transfer reactions from SNAP to four thiols are exothermic with entropy loss. The kinetic behavior of BSANO/RSH transfer can be related to both the acidity of sulfhydryl group and the electronic structure in thiol.
Studies Related to Thietan-2-ones. Part 1. Conversion of D-Penicillamine into DL-2-Methylpenicillamine using Thietan-2-one-based Chemistry
Al-Zaidi, Shakir M.R.,Crilley, Martine M. L.,Stoodley, Richard J.
, p. 2259 - 2266 (2007/10/02)
A series of N-substituted derivatives of (3R)-3-amino-4,4-dimethylthietan-2-one has been prepared from D-penicillamine (3).Attempts to effect the methylathion at position 3 of the N-acetyl (7a), N,N-diacetyl (12), N-benzyloxycarbonyl (7b), or N-(p-nitrobenzylidene) derivative (15a) were unrewarding.Although the N-benzylidene and N-furfurylidene derivatives (15b) and (15c) were successfully methylated at position 3 by using iodomethane and potassium t-butoxide in tetrahydrofuran (THF), best results were achieved by treating the N-(2-hydroxy-1-naphthylmethylene) derivative (15d) with iodomethane and sodium hydride in N,N-dimethylformamide.Cleavage of the imine linkage of the methylated derivatives of the thietanones (15c) and (15d), i.e. compounds (19b) and (19c), was effected by using, respectively, toluene-p-sulphonic acid in THF and dilute hydrochloric acid in acetone.The derived salts of (3RS)-3-amino-3,4,4-trimethylthietan-2-one, i.e. (21a) and (21b), underwent hydrolysis in boiling water to give the corresponding salts of DL-2-methylpenicillamine, i.e. (22a) and (22b).
