110755-32-3

Usage

Uses

Used in Organic Synthesis:
N-ALPHA-BOC-(R)-2-AMINO-3-(DIMETHYLAMINO)PROPIONIC ACID is used as a building block in organic synthesis for the preparation of peptide-based drugs and compounds. Its unique structure allows for the creation of complex molecules with specific biological activities.
Used as a Chiral Auxiliary:
In the field of asymmetric synthesis, N-ALPHA-BOC-(R)-2-AMINO-3-(DIMETHYLAMINO)PROPIONIC ACID is used as a chiral auxiliary. It aids in the synthesis of enantiomerically pure compounds, which is crucial for the development of pharmaceuticals with fewer side effects.
Used in the Introduction of Dimethylamino Group:
N-ALPHA-BOC-(R)-2-AMINO-3-(DIMETHYLAMINO)PROPIONIC ACID serves as a reagent for the introduction of the dimethylamino group in organic compounds. The dimethylamino group can enhance the solubility and reactivity of the resulting molecules, making them suitable for various applications.
Used as a Ligand in Metal-Catalyzed Asymmetric Reactions:
N-ALPHA-BOC-(R)-2-AMINO-3-(DIMETHYLAMINO)PROPIONIC ACID is also utilized as a ligand in metal-catalyzed asymmetric reactions. Its presence can improve the selectivity and efficiency of these reactions, leading to the production of enantiomerically enriched products.

Upstream product

• 50-00-0 formaldehyd 
• 76387-70-7 (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid 

Downstream Products

• 1416469-71-0 tert-butyl [(2R)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexa-hydrophthalazin-2(1H)-yl]piperidin-1-yl}-3-(dimethylamino)-1-oxopropan-2-yl]carbamate 
• 1416469-70-9 (4aS,8aR)-2-{1-[(2R)-2-amino-3-(dimethylamino)propanoyl]piperidin-4-yl}-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one trifluoroacetate 
• 1416469-84-5 (4aS,8aR)-2-{1-[(2S)-2-amino-3-(dimethylamino)propanoyl]piperidin-4-yl}-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one trifluoroacetate 
• 1416469-87-8 tert-butyl [(2S)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexa-hydrophthalazin-2(1H)-yl]piperidin-1-yl}-3-(dimethylamino)-1-oxopropan-2-yl]carbamate 
• 1422694-98-1 Boc-Dmaa-D-Pro-Aib-Phe-OMe 

Relevant academic research and scientific papers

Peptide Stapling with Anion-π Catalysts

We report design, synthesis and evaluation of a series of naphthalenediimides (NDIs) that are bridged with short peptides. Reminiscent of peptide stapling technologies, the macrocycles are conveniently accessible by a chromogenic nucleophilic aromatic substitution of two bromides in the NDI core with two thiols from cysteine sidechains. The dimension of core-bridged NDIs matches that of one turn of an α helix. NDI-stapled peptides exist as two, often separable atropisomers. Introduction of tertiary amine bases in amino-acid sidechains above the π-acidic NDI surface affords operational anion-π catalysts. According to an enolate chemistry benchmark reaction, anion-π catalysis next to peptides occurs with record chemoselectivity but weak enantioselectivity. Catalytic activity drops with increasing distance of the amine base to the NDI surface, looser homocysteine bridges, mismatched, shortened and elongated α-helix turns, and acyclic peptide controls. Elongation of isolated turns into short α helices significantly increases activity. This increase is consistent with remote control of anion-π catalysis from the α-helix macrodipole.

Phe*-Ala-based pentapeptide mimetics are BACE inhibitors: P2 and P3 SAR.

We describe herein the syntheses and evaluation of a series of C-termini pyridyl containing Phe*-Ala-based BACE inhibitors (5-19). In conjunction with four fixed residues at the P1 (Phe), P1' (Ala), P2' (Val), and P2' cap (Pyr.), rather detailed SAR modifications at P2 and P3 positions were pursued. The promising inhibitors emerging from this SAR investigation, 12 and 17 demonstrated very good enzyme potency (IC(50)=45 nM) and cellular activity (IC(50)=0.4 microM).