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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:
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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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K Aarstad et al.
European journal of biochemistry, 112(2), 335-338 (1980-11-01)
The amino acid analog L-cyclohexylalanine, which may be considered an analog of the hydrophobic amino acids leucine and valine, was found to thioester-bind to the heavy enzyme of gramicidin S synthetase. The results indicate that it preferably binds to the
Nathan A Schnarr et al.
Journal of the American Chemical Society, 125(3), 667-671 (2003-01-16)
Designed coiled-coil heterotrimers are described whose assembly is governed by both hydrophobic and hydrophilic forces. Sterically matched hydrophobic core side-chain packing of alanine and cyclohexylalanine has been shown to promote formation of a 1:1:1 heterotrimer. Manipulation of hydrophilic glutamic acid
Géza Tóth et al.
Journal of medicinal chemistry, 50(2), 328-333 (2007-01-19)
The opioid peptide TIPP (H-Tyr-Tic-Phe-Phe-OH, Tic:1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) was substituted with Dmt (2',6'-dimethyltyrosine) and a new unnatural amino acid, beta-MeCha (beta-methyl-cyclohexylalanine). This double substitution led to a new series of opioid peptides displaying subnanomolar delta antagonist activity and mu agonist or
J Hondrelis et al.
International journal of peptide and protein research, 37(1), 21-26 (1991-01-01)
Analogues of angiotensin II with cyclohexylalanine (Cha) at position 4 or 8, and analogues of the competitive (type II) angiotensin antagonist [Sar1,Tyr(Me)4]ANG II (Sarmesin) with Cha at position 8, have been prepared by the solid phase method and purified by
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
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