865799-12-8

Basic information

• Product Name: (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid
• CAS NO: 865799-12-8
• Molecular Weight: 143.186
• Mol File: 865799-12-8.mol

Chemical Properties

• CAS DataBase Reference: (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid(865799-12-8)
• EPA Substance Registry System: (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid(865799-12-8)

Safety Data

• Hazardous Substances Data: 865799-12-8(Hazardous Substances Data)

Upstream product

• 1017279-76-3 (1R,3S)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutan-1-carboxylic acid 
• 64396-97-0 (+)-cis-pinonic acid 
• 865799-08-2 (1S,3S)-N-[3-(2,2-diphenyl-2-hydroxyethyl)-2,2-dimethylcyclobutyl]acetamide 
• 865799-10-6 (1S,3S)-N-[3-(2,2-diphenylethenyl)-2,2-dimethylcyclobutyl]acetamide 
• 865799-11-7 (1R,3S)-3-acetamido-2,2-dimethylcyclobutane-carboxylic acid 
• 865799-14-0 (1S,3S)-methyl (3-acetamido-2,2-dimethylcyclobutyl)acetate 
• 865799-07-1 (-)-(1'S,3'S)-2-(3'-acetamido-2',2'-dimethylcyclobutyl)acetic acid 

Downstream Products

• 308287-86-7 (1R,3S)-3-amino-2,2-dimethylcyclobutylmethanol 

Relevant articles and documents

Synthesis of enantiopure cyclobutane amino acids and amino alcohols

(-)-(1R,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(1R,3S)-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1R)-α-pinen

Replacement of Thr32 and Gln34 in the C -terminal neuropeptide y fragment 25-36 by cis -cyclobutane and cis -cyclopentane β-amino acids shifts selectivity toward the Y4 receptor

Neuropeptide Y (NPY) and pancreatic polypeptide (PP) control central and peripheral processes by activating the G protein coupled receptors Y xR (x = 1, 2, 4, 5). We present analogs of the C-terminal fragments 25-36 and 32-36 of NPY and PP containing (1R,2S)-cyclobutane (βCbu) or (1R,2S)-cyclopentane (βCpe) β-amino acids, which display exclusively Y4R affinity. In particular, [βCpe34]-NPY-(25-36) is a Y4R selective partial agonist (EC50 41 ± 6 nM, Emax 71%) that binds Y4R with a Ki of 10 ± 2 nM and a selectivity >100-fold relative to Y1R and Y2R and >50-fold relative to Y5R. Comparably, [Y 32, βCpe34]-NPY(PP)-(32-36) selectively binds and activates Y4R (EC50 94 ± 21 nM, Emax 73%). The NMR structure of [βCpe34]-NPY-(25-36) in dodecylphosphatidylcholine micelles shows a short helix at residues 27-32, while the C-terminal segment R33βCpe34R35Y 36 is extended. The biological properties of the βCbu- or βCpe-containing NPY and PP C-terminal fragments encourage the future application of these β-amino acids in the synthesis of selective Y 4R ligands.