Cas no 59286-25-8 ((2R,3S)-3-Hydroxynorleucine)

(2R,3S)-3-Hydroxynorleucine is a non-proteinogenic amino acid characterized by its stereospecific hydroxyl group at the β-position of the norleucine backbone. This chiral compound serves as a valuable intermediate in organic synthesis and pharmaceutical research, particularly in the development of peptidomimetics and enzyme inhibitors. Its defined stereochemistry ensures high selectivity in asymmetric synthesis, while the hydroxyl group enhances its utility as a building block for modifying peptide properties, such as solubility and binding affinity. The compound’s structural features also make it suitable for studying metabolic pathways and amino acid analogs. Its purity and stability under standard conditions further support its application in rigorous experimental settings.
(2R,3S)-3-Hydroxynorleucine structure
(2R,3S)-3-Hydroxynorleucine structure
Product Name:(2R,3S)-3-Hydroxynorleucine
CAS No:59286-25-8
MF:C6H13NO3
MW:147.172322034836
CID:1612852
PubChem ID:13683856
Update Time:2025-06-08

(2R,3S)-3-Hydroxynorleucine Chemical and Physical Properties

Names and Identifiers

    • (2R,3S)-2-amino-3-hydroxyhexanoic acid
    • (2R,3S)-2-Amino-3-hydroxy-hexanoic acid
    • (+-)-erythro-2-amino-3-hydroxy-hexanoic acid
    • KB-61716
    • Threo-d-b-hydroxynorleucine
    • FT-0690334
    • (+-)-erythro-2-Amino-3-hydroxy-hexansaeure
    • (2R,3S)-3-HYDROXYNORLEUCINE
    • DTXSID80546658
    • (3S)-3-Hydroxy-D-norleucine
    • DB-214742
    • 59286-25-8
    • (2r,3s)-2-amino-3-hydroxyhexanoicAcid
    • (3S)-3-Hydroxy-D-norleucine; threo-3-Hydroxy-D-norleucine; (2R,3S)-2-amino-3-hydroxy-hexanoic Acid
    • (2R,3S)-3-Hydroxynorleucine
    • Inchi: 1S/C6H13NO3/c1-2-3-4(8)5(7)6(9)10/h4-5,8H,2-3,7H2,1H3,(H,9,10)/t4-,5+/m0/s1
    • InChI Key: ONTYPWROJNTIRE-CRCLSJGQSA-N
    • SMILES: O[C@H]([C@H](C(=O)O)N)CCC

Computed Properties

  • Exact Mass: 147.08954328g/mol
  • Monoisotopic Mass: 147.08954328g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 4
  • Complexity: 116
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.1
  • Topological Polar Surface Area: 83.6?2

(2R,3S)-3-Hydroxynorleucine Pricemore >>

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Additional information on (2R,3S)-3-Hydroxynorleucine

Exploring the Unique Properties and Applications of (2R,3S)-3-Hydroxynorleucine (CAS No. 59286-25-8)

In the realm of specialized amino acids, (2R,3S)-3-Hydroxynorleucine (CAS No. 59286-25-8) stands out as a compound of significant scientific and industrial interest. This stereospecific hydroxy amino acid derivative has garnered attention for its unique structural features and potential applications in pharmaceuticals, biotechnology, and nutritional research. As researchers increasingly focus on chiral building blocks and unnatural amino acids, compounds like 3-Hydroxynorleucine have become valuable tools in drug discovery and development.

The molecular structure of (2R,3S)-3-Hydroxynorleucine features both hydroxyl and amino functional groups at specific stereocenters, making it particularly interesting for peptide modification and protein engineering. Current trends in precision medicine and targeted therapies have driven demand for such specialized amino acids that can impart unique properties to therapeutic peptides. The compound's CAS registry number (59286-25-8) serves as a crucial identifier for researchers sourcing this material for their studies.

Recent scientific literature highlights the growing importance of hydroxylated amino acids in developing novel enzyme inhibitors and receptor modulators. The specific stereochemistry of (2R,3S)-3-Hydroxynorleucine makes it particularly valuable for creating conformationally constrained peptides, a hot topic in current drug design research. Pharmaceutical companies are actively investigating how such modified amino acids can improve the metabolic stability and bioavailability of peptide-based drugs.

In the field of biocatalysis and green chemistry, 59286-25-8 has emerged as an interesting substrate for enzymatic transformations. Researchers are exploring its use in asymmetric synthesis and as a precursor for more complex chiral compounds. The compound's hydroxyl group provides a handle for further chemical modifications, making it versatile for various synthetic applications while maintaining its stereochemical integrity.

The nutritional aspects of modified amino acids like 3-Hydroxynorleucine have also attracted attention in sports nutrition and metabolic research. While not a naturally occurring proteinogenic amino acid, its structural similarity to natural amino acids makes it an interesting candidate for studying amino acid transporters and metabolic pathways. However, comprehensive clinical studies would be needed to evaluate any potential nutritional applications.

From a synthetic chemistry perspective, the production of high-purity (2R,3S)-3-Hydroxynorleucine requires sophisticated chiral synthesis techniques. Manufacturers employ various strategies including asymmetric hydrogenation, enzymatic resolution, or chiral pool synthesis to obtain this compound with the required stereochemical purity. The demand for such precisely defined stereoisomers continues to grow as the pharmaceutical industry places greater emphasis on enantiopure drugs.

Analytical characterization of 59286-25-8 typically involves advanced techniques such as chiral HPLC, NMR spectroscopy, and mass spectrometry to confirm both chemical identity and stereochemical purity. These quality control measures are essential given the compound's potential use in pharmaceutical development, where even minor stereochemical impurities could significantly impact biological activity.

Looking toward future applications, researchers are investigating how (2R,3S)-3-Hydroxynorleucine might contribute to the development of peptide therapeutics for metabolic disorders and other conditions. Its unique structure could help address common challenges in peptide drug development, such as improving membrane permeability and proteolytic stability. As the field of peptidomimetics continues to evolve, compounds like this hydroxy amino acid derivative will likely play increasingly important roles.

In conclusion, (2R,3S)-3-Hydroxynorleucine (CAS No. 59286-25-8) represents a valuable addition to the toolbox of synthetic and medicinal chemists. Its unique stereochemical features and functional group arrangement make it particularly interesting for current research trends in drug discovery, peptide engineering, and biocatalysis. As scientific understanding of modified amino acids continues to grow, so too will the potential applications of this specialized compound in various fields of chemistry and biology.

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