73397-25-8

Usage

Uses

Used in Pharmaceutical Synthesis:
BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID is used as a reagent/building block for the preparation of bestatin and its derivatives from natural and unnatural N-Boc-D-amino acids. Bestatin is a known PfA-M1 inhibitor, which has potential applications in the development of drugs targeting specific biological pathways.
Used in Research and Development:
In the field of medicinal chemistry, BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID serves as a valuable intermediate for the synthesis of novel compounds with potential therapeutic properties. Its unique stereochemistry and functional groups make it an attractive candidate for the development of new drugs and pharmaceutical agents.
Used in Chiral Synthesis:
Due to its chiral nature, BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID is used in the synthesis of enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals, agrochemicals, and fragrances. The ability to produce chiral compounds with high selectivity is crucial for the development of effective and safe drugs.
Used in Peptide Synthesis:
BOC-(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID can be employed in the synthesis of peptides and peptidomimetics, which are important in the development of new therapeutic agents, particularly in the area of protein-targeting drugs. Its protected amino group allows for the stepwise assembly of peptide chains, facilitating the synthesis of complex peptide structures.

Upstream product

• 73397-29-2 (2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid Methyl Ester 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 70853-26-8 (R)-4-methyl-1-oxopentane-2-benzylcarbamate 
• 63219-62-5 [(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 62023-30-7 (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid 
• 73397-25-8 (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 73397-22-5 Cbz-D-Leu-OMe 
• 875322-16-0 C₁₂H₂₃NO₂ 
• 62023-30-7 DL-threo-3-amino-2-hydroxy-5-methylhexanoic acid 

Downstream Products

• 318464-20-9 (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid 
• 73397-20-3 (2S,3S)-3-Amino-2-hydroxy-5-methylhexanoic Acid 
• 73397-27-0 (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-methylhexanoic acid 
• 73397-34-9 (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester 
• 73465-22-2 (2R,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester 
• 73397-26-9 (2R,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 73465-23-3 (2R,3R)-(3-Amino-2-hydroxy-5-methylhexanoyl)-L-valyl-L-valyl-L-aspartic Acid 
• 67655-94-1 amastatin 

Relevant academic research and scientific papers

Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase

The malarial PfA-M1 metallo-aminopeptidase is considered a putative drug target. The natural product dipeptide mimetic, bestatin, is a potent inhibitor of PfA-M1. Herein we present a new, efficient, and high-yielding protocol for the synthesis of bestatin derivatives from natural and unnatural N-Boc-d-amino acids. A diverse library of bestatin derivatives was synthesized with variants at the side chain of either the α-hydroxyβ-amino acid (P1) or the adjacent naturalα-amino acid (P1′). Surprisingly, we found that extended aromatic side chains at the P1 position resulted in potent inhibition against PfA-M1. To understand these data, we determined the X-ray cocrystal structures of PfA-M1 with two derivatives having either a Tyr(OMe) 15 or Tyr(OBzl) 16 at the P1 position and observed substantial inhibitor-induced rearrangement of the primary loop within the PfA-M1 pocket that interacts with the P1 side chain. Our data provide important insights for the rational design of more potent and selective inhibitors of this enzyme that may eventually lead to new therapies for malaria.

Synthesis of (2S,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid Derivatives. Application to the Synthesis of Amastatin, an Inhibitor of Aminopeptidases

Methods are reported for the synthesis of optically pure derivatives of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid. -D-leucine methyl ester was reduced in 95percent yield with diisobutylaluminum hydride to the aldehyde which was converted via the cyanohydrin to (2RS,3R)-3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA).The mixture of diastereomers was converted to the corresponding Boc-AHMHA methyl ester derivatives and separated by chromatography over silica gel.The optical purity of the diastereomers at C-3 was established by converting each to diastereomeric Boc-AHMHA-Leu-OMe and separating these dipeptides by chromatography.Pure (2S,3R)-Boc-AHMHA was coupled with valyl-valyl-aspartic acid dibenzyl ester by using dicyclohexylcarbodiimide/ 1-hydroxybenzotriazole in 63percent yield.The Boc group was removed by using trifluoroacetid acid, and the benzyl groups were removed by hydrogenolysis.The product, (2S,3R)-AHMHA-L-Val-L-Val-L-Asp, amastatin, was found to be identical with the natural product.