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29295

Sigma-Aldrich

3-Cyclohexyl-D-alanine hydrate

≥99.0% (calc. based on dry substance, NT), ~1 mol/mol water

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About This Item

Empirical Formula (Hill Notation):
C9H17NO2 · xH2O
CAS Number:
58717-02-5
Molecular Weight:
171.24 (anhydrous basis)
Beilstein/REAXYS Number:
3197315
MDL number:
MFCD00217056
UNSPSC Code:
12352200
PubChem Substance ID:
57648357
NACRES:
NA.22

assay

≥99.0% (calc. based on dry substance, NT)

form

solid

optical activity

[α]20/D −12±1°, c = 1% in 1 M HCl (dry matter)

impurities

~1 mol/mol water

application(s)

peptide synthesis

SMILES string

O.N[C@H](CC1CCCCC1)C(O)=O

InChI

1S/C9H17NO2.H2O/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h7-8H,1-6,10H2,(H,11,12);1H2/t8-;/m1./s1

InChI key

HDJQIWAIDCEDEF-DDWIOCJRSA-N

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Tuning wasp toxin structure for nicotinic receptor antagonism: cyclohexylalanine-containing analogues as potent and voltage-dependent blockers.
Christian A Olsen et al.
ChemMedChem, 1(3), 303-305 (2006-08-08)
Chad D Tatko et al.
Journal of the American Chemical Society, 126(7), 2028-2034 (2004-02-20)
We have examined the impact of C-H...pi and hydrophobic interactions in the diagonal position of a beta-hairpin peptide through comparison of the interaction of Phe, Trp, or Cha (cyclohexylalanine) with Lys or Nle (norleucine). NMR studies, including NOESY and chemical
Nathan A Schnarr et al.
Journal of the American Chemical Society, 124(33), 9779-9783 (2002-08-15)
Specific coiled-coil heterotrimers result from steric matching of hydrophobic core side chains. A 2:1 heterotrimer is formed by peptides containing alanine or cyclohexylalanine, respectively, at a central core residue. Detailed thermodynamic analysis reveals that the designed complex is considerably more
Christopher J Pace et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(19), 5832-5836 (2012-04-05)
CH-π stacks up! Using the protein α(2) D as a model system, we estimate that a CH-π contact between cyclohexylalanine (Cha) and phenylalanine (F) contributes approximately -0.7 kcal  mol(-1) to the protein stability. The stacking F-Cha pairs are sequestered in the
Jong Hoon Kim et al.
FEMS microbiology letters, 276(1), 93-98 (2007-10-17)
New derivatives of monascus pigment were produced during Monascus fermentation by the addition of unnatural amino acids, and the inhibitory activities of the derivatives against diet-related lipase and alpha-glucosidase were tested. Derivatives with penicillamine (H-Pen), cyclohexylalanine (H-Cha), butylglycine (L-t-Bg), and
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