cis-4-Aminocyclohexanecarboxylic acid
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cis-4-Aminocyclohexanecarboxylic acid

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Category
γ−Amino acids
Catalog number
BAT-006848
CAS number
3685-23-2
Molecular Formula
C7H13NO2
Molecular Weight
143.19
cis-4-Aminocyclohexanecarboxylic acid
IUPAC Name
4-aminocyclohexane-1-carboxylic acid
Synonyms
H-cis-NH(4)cHex-OH
Appearance
White solid
Purity
≥ 95% (NMR)
Melting Point
299-301 °C(lit.)
Boiling Point
280°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C7H13NO2/c8-6-3-1-5(2-4-6)7(9)10/h5-6H,1-4,8H2,(H,9,10)
InChI Key
DRNGLYHKYPNTEA-OLQVQODUSA-N
Canonical SMILES
C1CC(CCC1C(=O)O)N
1.Identification of novel classes of protein kinase inhibitors using combinatorial peptide chemistry based on functional genomics knowledge.
Lukas TJ1, Mirzoeva S, Slomczynska U, Watterson DM. J Med Chem. 1999 Mar 11;42(5):910-9.
A discovery approach based on an intramolecular inhibitory mechanism was applied to a prototype calmodulin (CaM)-regulated protein kinase in order to demonstrate a proof-of-principle for the development of selective inhibitors. The overall approach used functional genomics analysis of myosin light chain kinase (MLCK) to identify short autoinhibitory sequences that lack CaM recognition activity, followed by recursive combinatorial peptide library production and comparative activity screens. Peptide 18 (Arg-Lys-Lys-Tyr-Lys-Tyr-Arg-Arg-Lys-NH2), one of several selective inhibitors discovered, has an IC50 = 50 nM for MLCK, inhibits CaM kinase II only at 4000-fold higher concentrations, and does not inhibit cyclic AMP-dependent protein kinase. Analogues of peptide 18 containing conformationally constrained cis-4-aminocyclohexanecarboxylic acid retained affinity and selectivity. The inhibitors add to the armamentarium available for the deconvolution of complex signal transduction pathways and their relationship to homeostasis and disease, and the approach is potentially applicable to enzymes in which the catalytic and regulatory domains are found within the same open reading frame of a cDNA.
2.cis-4-[[[(2-Chloroethyl)nitrosoamino]carbonyl]methylamino] cyclohexanecarboxylic acid, a nitrosourea with latent activity against an experimental solid tumor.
Johnston TP, McCaleb GS, Rose WC, Montgomery JA. J Med Chem. 1984 Jan;27(1):97-9.
cis-4-[[[(2-Chloroethyl)nitrosoamino]carbonyl]methylamino] cyclohexanecarboxylic acid (N-Me-cis-CCCNU) was synthesized in five steps from cis-4-aminocyclohexanecarboxylic acid via an N-tosylated intermediate. N-Me-cis-CCCNU, which is incapable of the facile decomposition that characterizes the clinically useful nitrosoureas, effected a significant cure rate of both early and established murine Lewis lung carcinoma, even though its in vitro half-life was approximately 5.5 times that of the unmethylated parent compound. This is the first observation of latent activity of a nitrosourea against an experimental solid tumor.
3.Influence of conformationally constrained amino acids replacing positions 2 and 3 of arginine vasopressin (AVP) and its analogues on their pharmacological properties.
Sobolewski D1, Prahl A, Derdowska I, Kwiatkowska A, Slaninová J, Lammek B. Protein Pept Lett. 2007;14(3):213-7.
Synthesis of thirteen new analogues of arginine vasopressin (AVP) has been described. Amino acid residues at positions 2 and 3 of AVP, [3-mercaptopropionic acid (Mpa)(1)]AVP (dAVP), [Mpa(1),d-Arg(8)]VP (dDAVP) and [Mpa(1),Val(4),d-Arg(8)]VP (dVDAVP) were replaced with one amino acid residue using sterically constrained non-proteinogenic amino acids, 4-aminobenzoic acid (Abz), cis-4-aminocyclohexanecarboxylic acid (ach) or its trans-isomer (Ach). In the case of a potent V(1a) antagonist, [1-mercaptocyclohexaneacetic acid (Cpa)(1)]AVP, only one similar analogue has been prepared by replacing positions 2 and 3 with Abz. Unfortunately, all new peptides were inactive in bioassays for the pressor, antidiuretic and uterotonic in vitro activities in the rat.
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