Fmoc-trans-4-aminocyclohexane carboxylic acid
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Fmoc-trans-4-aminocyclohexane carboxylic acid

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Category
Fmoc-Amino Acids
Catalog number
BAT-007494
CAS number
147900-46-7
Molecular Formula
C22H23NO4
Molecular Weight
365.42
Fmoc-trans-4-aminocyclohexane carboxylic acid
IUPAC Name
4-(9H-fluoren-9-ylmethoxycarbonylamino)cyclohexane-1-carboxylic acid
Synonyms
Fmoc-1,4-trans-Achc-OH; Fmoc-trans-4-aminocyclohexane-1-carboxylic acid
Appearance
White crystalline powder
Purity
≥ 99% (HPLC)
Melting Point
210-217 °C (dec.)
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H23NO4/c24-21(25)14-9-11-15(12-10-14)23-22(26)27-13-20-18-7-3-1-5-16(18)17-6-2-4-8-19(17)20/h1-8,14-15,20H,9-13H2,(H,23,26)(H,24,25)
InChI Key
RIZQTCLNVHZQOO-UHFFFAOYSA-N
Canonical SMILES
C1CC(CCC1C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
1. Phenanthrene-4-carboxylic acid and 1,2-dihydrophenanthrene-4-carboxylic acid
L J Fitzgerald, R E Gerkin Acta Crystallogr C. 1998 Jul 15;54 ( Pt 7):966-9. doi: 10.1107/s0108270198000122.
Phenanthrene-4-carboxylic acid, C15H10O2, crystallized in the centrosymmetric space group P2(1)/n, while 1,2-dihydrophenanthrene-4-carboxylic acid, C15H12O2, crystallized in the centrosymmetric space group Pbca. In each structure, there is a single type of hydrogen bond: it is of the cyclic dimer type about a center of symmetry. The Odonor...Oacceptor distances are 2.634 (2) and 2.651 (2) A, and the O-H...O angles are 176 (3) and 173 (2) degrees, respectively, for the two structures. In each structure, the carboxy H and O atoms are ordered. The phenanthrene core of the fully aromatic acid is roughly planar; the dihedral angle between the best-fit core plane and the carboxy group plane is 63.7 (1) degree. As expected, the hydrogenated ring of the second acid is much less nearly planar; the remaining naphthalenoid core is, however, roughly planar and the dihedral angle between this best-fit plane and the carboxy group plane is 60.4 (1) degree.
2. Directing carboxylic acid dehydrogenation
Yoshiharu Iwabuchi Science. 2021 Dec 3;374(6572):1199. doi: 10.1126/science.abm4457. Epub 2021 Dec 2.
A palladium ligand can activate carbon-hydrogen bonds yet avoid product olefin reactions.
3. Carboxylic acid reductases in metabolic engineering
Neil Butler, Aditya M Kunjapur J Biotechnol. 2020 Jan 10;307:1-14. doi: 10.1016/j.jbiotec.2019.10.002. Epub 2019 Oct 16.
Carboxylic acid reductases (CARs) catalyze the conversion of carboxylic acids to aldehydes, which are a valuable class of chemicals for many consumer and industrial applications. CARs generally exhibit broad substrate specificity that encompasses aromatic, aliphatic, and di/tri-carboxylic acids, enabling the development of biosynthetic pathways to a wide array of potential aldehyde products. De novo synthetic pathways implementing CARs have enabled the production of sustainable aldehyde products or utilized highly reactive aldehydes as intermediates in the production of chemicals including amines, alcohols, and alkanes. Recent determination of crystal structures of the domains of three CARs has provided insight into the substrate binding and domain dynamics of CARs, which could enable future engineering efforts to both alter the specificity of CAR and expand its potential in future synthetic pathways. In this review, we summarize the current structural and mechanistic understanding of CARs including substrate and catalytic scope, their potential for future engineering, and the advantages and challenges of their application in de novo synthesis.
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