404853
cis-4-Aminocyclohexanecarboxylic acid
95%
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About This Item
Linear Formula:
H2NC6H10CO2H
CAS Number:
Molecular Weight:
143.18
PubChem Substance ID:
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
2802522
MDL number:
SMILES string
N[C@H]1CC[C@H](CC1)C(O)=O
InChI
1S/C7H13NO2/c8-6-3-1-5(2-4-6)7(9)10/h5-6H,1-4,8H2,(H,9,10)/t5-,6+
InChI key
DRNGLYHKYPNTEA-OLQVQODUSA-N
assay
95%
form
powder
mp
299-301 °C (lit.)
General description
cis-4-aminocyclohexanecarboxylic acid (C4-ACHC, cis-ACCA) exists in zwitterionic form. Cyclohexane ring in the molecule of cis-4-aminocyclohexanecarboxylic acid is present in chair conformation. The carboxylate and ammonium groups in the molecule occupy axial and equatorial positions, respectively. It co-crystallizes with water molecules in a 2:1 (amino acid:water ratio). H-Cys-Leu-Gly-Gly-Leu-Leu-Thr-Met-Val-OH (CLG) peptide analogue containing cis-ACCA has been prepared and its activity has been studied.
Application
cis-4-Aminocyclohexanecarboxylic acid may be used in the synthesis of new analogs of arginine vasopressin (AVP). It may be used in the synthesis of cis-4-[[[(2-chloroethyl)nitrosoamino]carbonyl]methylamino]cyclohexanecarboxylic acid.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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T P Johnston et al.
Journal of medicinal chemistry, 27(1), 97-99 (1984-01-01)
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
Hydrogen-bonding patterns in cis-4-ammoniocyclohexanecarboxylate hemihydrate.
Edward E Avila et al.
Acta crystallographica. Section C, Crystal structure communications, 60(Pt 10), o759-o761 (2004-10-07)
S K Lo et al.
Journal of applied physiology (Bethesda, Md. : 1985), 58(5), 1421-1427 (1985-05-01)
We examined the effect of fibrinolysis depression on thrombin-induced pulmonary microembolism in awake sheep prepared with chronic lung lymph fistulas. Fibrinolysis was depressed by an intravenous infusion (100 mg) of tranexamic acid [trans-4-(Aminomethyl)cyclohexanecarboxylic acid]. Pulmonary microembolism was induced by an
Dariusz Sobolewski et al.
Protein and peptide letters, 14(3), 213-217 (2007-03-10)
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
Mauro Marastoni et al.
Bioorganic & medicinal chemistry, 10(9), 3061-3066 (2002-07-12)
In order to improve the immunotherapeutical potential of H-Cys-Leu-Gly-Gly-Leu-Leu-Thr-Met-Val-OH (CLG) peptide, an Epstein-Barr virus (EBV) subdominant epitope derived from the membrane protein LMP2, we have synthesized and tested CLG analogues containing cis- and/or trans-4-aminocyclohexanecarboxylic acid (ACCA) replacing Gly-Gly and/or Thr-Met
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