327-56-0 Usage
Description
D-Norleucine, also known as (2S,3S)-2-amino-3-methylpentanoic acid, is a non-proteinogenic amino acid with a chiral center. It is an isomer of the naturally occurring L-leucine and exhibits unique properties due to its distinct stereochemistry. D-Norleucine is a promising building block for the synthesis of various bioactive compounds and pharmaceuticals.
Source:
D-Norleucine can be synthesized through various chemical and enzymatic methods, including asymmetric synthesis, enzymatic resolution, and biotransformation processes.
Production Methods:
D-Norleucine can be produced by enzymatic resolution using D-amino acid oxidase, which selectively oxidizes D-amino acids, or through asymmetric synthesis using chiral catalysts or auxiliaries. Biotransformation methods involving microorganisms or isolated enzymes can also be employed for the production of D-Norleucine.
Uses
Used in Pharmaceutical Industry:
D-Norleucine is used as a key intermediate in the synthesis of Thailandepsin B, a bicyclic depsipeptide histone deacetylase (HDAC) inhibitor. HDAC inhibitors have gained significant attention due to their potential as therapeutic agents for the treatment of various diseases, including cancer and neurodegenerative disorders. Thailandepsin B, in particular, has shown promising anticancer activity by modulating gene expression and inducing cell cycle arrest and apoptosis in cancer cells.
Additionally, D-Norleucine can be utilized in the development of other bioactive compounds and pharmaceuticals, given its unique structural features and potential for further functionalization. Its chiral nature allows for the exploration of novel stereoselective reactions and the synthesis of enantiomeric compounds with distinct biological activities.
Purification Methods
Crystallise norleucine from water or aqueous MeOH. [Huffman & Ingersoll J Am Chem Soc 73 3366 1951, Beilstein 4 III 1386, 4 IV 2628.]
Check Digit Verification of cas no
The CAS Registry Mumber 327-56-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,2 and 7 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 327-56:
(5*3)+(4*2)+(3*7)+(2*5)+(1*6)=60
60 % 10 = 0
So 327-56-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m1/s1
327-56-0Relevant articles and documents
One-Pot Preparation of d-Amino Acids Through Biocatalytic Deracemization Using Alanine Dehydrogenase and Ω-Transaminase
Han, Sang-Woo,Shin, Jong-Shik
, p. 3678 - 3684 (2018/10/20)
d-Amino acids are pharmaceutically important building blocks, leading to a great deal of research efforts to develop cost-effective synthetic methods. Preparation of d-amino acids by deracemization has been conceptually attractive owing to facile synthesis of racemic amino acids by Strecker synthesis. Here, we demonstrated biocatalytic deracemization of aliphatic amino acids into d-enantiomers by running cascade reactions; (1) stereoinversion of l-amino acid to a d-form by amino acid dehydrogenase and ω-transaminase and (2) regeneration of NAD+ by NADH oxidase. Under the cascade reaction conditions containing 100?mM isopropylamine and 1?mM NAD+, complete deracemization of 100?mM dl-alanine was achieved after 24?h with 95% reaction yield of d-alanine (> 99% eeD, 52% isolation yield). Graphical Abstract: [Figure not available: see fulltext.].
Nitrilases
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Paragraph 0495, (2015/09/22)
The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition, methods of designing new nitrilases and methods of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.
A green and expedient synthesis of enantiopure diketopiperazines via enzymatic resolution of unnatural amino acids
Pereira, Pedro C.,Arends, Isabel W.C.E.,Sheldon, Roger A.
supporting information, p. 4991 - 4993 (2015/01/09)
Dipeptides comprising a d-phenylglycyl moiety coupled to the l-enantiomer of 2-amino butyric acid, norvaline, norleucine, and homocysteine were successfully synthesized from d-phenylglycine amide and the racemate of the corresponding unnatural amino acid.
