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Showing NP-Card for 1-Amino-1-cyclohexanecarboxylic acid (NP0002878)

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Record Information
Version2.0
Created at2020-11-23 19:42:38 UTC
Updated at2021-08-12 19:52:24 UTC
NP-MRD IDNP0002878
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Amino-1-cyclohexanecarboxylic acid
Provided ByBMRBBMRB logo
Description1-Aminocyclohexanecarboxylic acid, also known as 1-azanylcyclohexane-1-carboxylate, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 1-Amino-1-cyclohexanecarboxylic acid was first documented in 1983 (PMID: 6847699). Based on a literature review a small amount of articles have been published on 1-Aminocyclohexanecarboxylic acid (PMID: 3346675) (PMID: 24039017) (PMID: 18821748).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.7691   -1.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732    0.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260    1.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    0.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546    0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713    1.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -2.1761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -1.2063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5652    0.8911    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -1.8733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702   -2.7775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -2.6739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1023   -1.5384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.6434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    1.2741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187    2.0654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9560    2.8474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    2.7438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    1.5988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  1
  6 15  1  0
  7 16  1  1
  7 17  1  0
  8 18  1  6
  8 19  1  0
  9 20  1  6
  9 21  1  0
 10 22  1  1
 10 23  1  0
M  END
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3D MOL for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

NP0002878
     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.0214   -0.2952    1.2569 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -0.1917   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902   -0.2987   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154   -0.2425   -2.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513   -0.4752   -0.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006   -1.2158   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308   -1.0291    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    0.3486    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027    1.4448    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2236    1.1740   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -0.0164    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -1.1595    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    0.3563    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385   -1.1081   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616   -2.2560   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.3596    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2507   -1.7282   -0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292    0.5076   -0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.4321    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    2.3753   -0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    1.7114    1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668    1.9667   -0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588    1.0589   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
M  END
Download

3D SDF for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.7691   -1.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732    0.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260    1.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    0.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546    0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713    1.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -2.1761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -1.2063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5652    0.8911    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -1.8733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702   -2.7775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -2.6739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1023   -1.5384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.6434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    1.2741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187    2.0654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9560    2.8474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    2.7438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    1.5988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  1
  6 15  1  0
  7 16  1  1
  7 17  1  0
  8 18  1  6
  8 19  1  0
  9 20  1  6
  9 21  1  0
 10 22  1  1
 10 23  1  0
M  END
> <DATABASE_ID>
NP0002878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1(CCCCC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO2/c8-7(6(9)10)4-2-1-3-5-7/h1-5,8H2,(H,9,10)

> <INCHI_KEY>
WOXWUZCRWJWTRT-UHFFFAOYSA-N

> <FORMULA>
C7H13NO2

> <MOLECULAR_WEIGHT>
143.1836

> <EXACT_MASS>
143.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.07772667266025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-aminocyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-1.3824455202126407

> <ALOGPS_LOGS>
-0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5651725232554874

> <JCHEM_PKA_STRONGEST_BASIC>
9.825359221511077

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
37.0574

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-aminocyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

NP0002878
     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.0214   -0.2952    1.2569 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -0.1917   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902   -0.2987   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154   -0.2425   -2.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513   -0.4752   -0.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006   -1.2158   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308   -1.0291    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    0.3486    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027    1.4448    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2236    1.1740   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334   -0.0164    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -1.1595    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    0.3563    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385   -1.1081   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616   -2.2560   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.3596    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2507   -1.7282   -0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292    0.5076   -0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.4321    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    2.3753   -0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    1.7114    1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668    1.9667   -0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588    1.0589   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
M  END
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PDB for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    7    9   10                                                  
CONECT    7    4    5    6    8                                             
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

COMPND    NP0002878
HETATM    1  N1  UNL     1       1.021  -0.295   1.257  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.821  -0.192  -0.155  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.090  -0.299  -0.867  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.215  -0.242  -2.116  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.251  -0.475  -0.130  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.201  -1.216  -0.598  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.431  -1.029   0.236  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.997   0.349   0.203  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.003   1.445   0.347  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.224   1.174  -0.503  1.00  0.00           C  
HETATM   11  H1  UNL     1       0.233  -0.016   1.845  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.509  -1.160   1.505  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.732   0.356   0.218  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.439  -1.108  -1.659  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.162  -2.256  -0.420  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.189  -1.360   1.266  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.251  -1.728  -0.103  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.629   0.508  -0.697  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.712   0.432   1.073  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.467   2.375  -0.089  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.750   1.711   1.390  1.00  0.00           H  
HETATM   22  H12 UNL     1       0.967   1.967  -0.449  1.00  0.00           H  
HETATM   23  H13 UNL     1      -0.159   1.059  -1.555  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    6   10
CONECT    3    4    4    5
CONECT    5   13
CONECT    6    7   14   15
CONECT    7    8   16   17
CONECT    8    9   18   19
CONECT    9   10   20   21
CONECT   10   22   23
END
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SMILES for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

NC1(CCCCC1)C(O)=O
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INCHI for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

InChI=1S/C7H13NO2/c8-7(6(9)10)4-2-1-3-5-7/h1-5,8H2,(H,9,10)
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Synonyms
ValueSource
1-Azanylcyclohexane-1-carboxylic acidChEBI
alpha-Aminocyclohexanecarboxylic aicdChEBI
1-Azanylcyclohexane-1-carboxylateGenerator
a-Aminocyclohexanecarboxylic aicdGenerator
Α-aminocyclohexanecarboxylic aicdGenerator
1-AminocyclohexanecarboxylateGenerator
1-Amino-1-cyclohexanecarboxylateHMDB
1-Aminocyclohexane-1-carboxylic acidHMDB
1-Aminocyclohexanecarboxylic acid, 14C-labeledHMDB
1-Aminocyclohexanecarboxylic acidChEBI
Chemical FormulaC7H13NO2
Average Mass143.1836 Da
Monoisotopic Mass143.09463 Da
IUPAC Name1-aminocyclohexane-1-carboxylic acid
Traditional Name1-aminocyclohexane-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
NC1(CCCCC1)C(O)=O
InChI Identifier
InChI=1S/C7H13NO2/c8-7(6(9)10)4-2-1-3-5-7/h1-5,8H2,(H,9,10)
InChI KeyWOXWUZCRWJWTRT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-1.4ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.06 m³·mol⁻¹ChemAxon
Polarizability15.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0243822
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1325
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1366
PDB IDNot Available
ChEBI ID86534
Good Scents IDNot Available
References
General References
  1. Aoyagi M, Agranoff BW, Washburn LC, Smith QR: Blood-brain barrier transport of 1-aminocyclohexanecarboxylic acid, a nonmetabolizable amino acid for in vivo studies of brain transport. J Neurochem. 1988 Apr;50(4):1220-6. doi: 10.1111/j.1471-4159.1988.tb10596.x. [PubMed:3346675 ]
  2. Lombardini JB, Sufrin JR: Chemotherapeutic potential of methionine analogue inhibitors of tumor-derived methionine adenosyltransferases. Biochem Pharmacol. 1983 Feb 1;32(3):489-95. doi: 10.1016/0006-2952(83)90528-2. [PubMed:6847699 ]
  3. Akagawa K, Sen J, Kudo K: Peptide-catalyzed regio- and enantioselective reduction of alpha,beta,gamma,delta-unsaturated aldehydes. Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11585-8. doi: 10.1002/anie.201305004. Epub 2013 Sep 5. [PubMed:24039017 ]
  4. Long YQ, Xue T, Song YL, Liu ZL, Huang SX, Yu Q: Synthesis and utilization of chiral alpha-methylated alpha-amino acids with a carboxyalkyl side chain in the design of novel Grb2-SH2 peptide inhibitors free of phosphotyrosine. J Med Chem. 2008 Oct 23;51(20):6371-80. doi: 10.1021/jm800487r. Epub 2008 Sep 27. [PubMed:18821748 ]