Amino Acids and Derivatives

Amino acids and their derivatives belong to a compound containing both amino group and carboxyl group. They are presented in both the form of free-state and bound-state in vivo. Free amino acids are distributed in all kinds of animal cells and body fluids with the bound amino acids being the mainly basic components of proteins and peptides.

Natural amino acids act as colorless crystalline materials with relatively high melting points being mostly above 200 ℃. They are usually soluble in water but insoluble in non-polar organic solvents. However, tyrosine and cystine are insoluble in water; proline and hydroxyl proline are soluble in ethanol and ether. All amino acids are soluble in strong acid and alkali solution.

According to the polar characterization of the R group of the side chain of the α-amino acid; those 20 common amino acids that constitute protein can be divided into four groups:
① Amino acids with R group being non-polar; There are 8 kinds in total, wherein five kinds have aliphatic side chains, namely alanine, leucine, isoleucine, valine and proline; two kinds are aromatic amino acids, phenylalanine and tryptophan; one kind belongs to sulfur-containing amino acid, namely methionine; amino acids belonging to this group have lower water solubility than polar R-group amino acid; proline is generally different with α-amino acid, it is formed through the substitution of one hydrogen atom of the amino acid with the side chains of the α- amino acid, belonging actually to imino acid.
② Amino acids with polar but non-charged R group; There are seven kinds in total, namely serine, threonine and tyrosine with R group having hydroxy group; cysteine with R group having a mercapto group of cysteine; glutamine and asparagine with R-group containing amide group, another amino acid is glycine ; glycine molecule has no R group, but having certain polarity, and thus being classified into this group; the side chains in this group of amino acid contain unassociated polar groups and can form hydrogen bonds with water, and is easily soluble in water.
③Amino acids with R group being positively charged amino acids. There are three kinds in total, namely, lysine, arginine, and histidine; they carry positive charge at pH7.0 and are also known as alkaline amino acids.
④Amino acids with R group being negatively charged. There are two kinds in total, namely glutamate and aspartate; at pH7.0, the molecules are negatively charged, also known as acidic amino acids. The formula, abbreviations symbols and related constants of 20 kinds of amino acid structures can be seen from the table. In addition to the 20 common amino acids mentioned above, there are also diiodotyrosine, thyroxine, hydroxyproline and hydroxylysine existing in certain proteins. In addition to amino acids involved in protein composition, it has been also found of more than 200 kinds of other kinds amino acids in a variety of tissues and cells; these amino acids are mostly derivatives of those α- amino acid composition of proteins.

However, there are some β-, γ- or δ- amino acids and some amino acids belong to D-type amino acids such as [beta]-alanine, [gamma]-aminobutyric acid and the phenylalanine contained in the antibiotics gramicidin-S, the D-alanine and D-glutamate contained in Gram-positive bacteria cell wall. Some non-protein amino acids can act as metabolically important precursors or intermediates, wherein β-alanine is the precursors of vitamin pantothenic acid; ornithine, and citrulline are the precursors in the synthesis of arginine; [gamma]-aminobutyric acid is the chemical neurotransmitter. Plants contain a large amount of non-protein amino acids, belonging to plant secondary substances, such as theanine, canavanine, djenkolic acid, β- Cyanoalanine and so on.

In addition to 20 kinds of amino acids found in the body and animal protein products, it has been found of nearly 200 kinds of other kinds of amino acids in nature. Most of them have been discovered in the plant kingdom and have complex molecular structures with no relation with the protein metabolism. There have been less that have been seen in the animal kingdom with some of them being originated from the chemical modification of certain incorporated amino acids in the specific proteins, for example, the proline and lysine contained in collagen protein are often partially subject to re-hydroxylation of hydroxyproline and hydroxylysine; Another example is that there are often a small amount of lysine and histidine contained in actin and myosin protein containing hypermethylated εN methyl-lysine and 3N-histidine; it has been also found in the histone protein that the ∈ amino group contained in lysine is acetylated and the OH group in the serine is phosphorylated; thyroglobulin contains iodinated tyrosine and thyronine iodide; The heavy chain of τ myosin and the N-terminal of certain proteins contain pyroglutamate formed by glutamine; there also exists the cystine constituting of two cysteine molecules in the general protein.

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Structure Chemical Name CAS MF
Z-LYS-OME HCL Z-LYS-OME HCL 26348-68-5 C15H23ClN2O4
3-IODO-L-THYRONINE 3-IODO-L-THYRONINE 10468-90-3 C15H14INO4
N-ME-VAL-OBZL P-TOSYLATE N-ME-VAL-OBZL P-TOSYLATE 42492-62-6 C13H19NO2
BZL-ALA-OME HCL BZL-ALA-OME HCL 19460-85-6 C11H16ClNO2
L-Serinamide hydrochloride L-Serinamide hydrochloride 65414-74-6 C3H9ClN2O2
EC 3.4.13.9 EC 3.4.13.9 9025-32-5
METHYL 6-(ACETYLAMINO)NICOTINATE METHYL 6-(ACETYLAMINO)NICOTINATE 98953-23-2 C9H10N2O3
BOC-D-ABU-OH BOC-D-ABU-OH 45121-22-0 C9H17NO4
FMOC-GLU-OFM FMOC-GLU-OFM 200616-18-8 C34H29NO6
FMOC-D-HIS-OH FMOC-D-HIS-OH 157355-79-8 C21H19N3O4
GLYCINE, [1-14C] GLYCINE, [1-14C] 56-39-3 C2H5NO2
AC-D-TYR-OH AC-D-TYR-OH 19764-32-0 C11H13NO4
N-(4-NITROBENZOYL)-L-GLUTAMIC ACID DIETHYL ESTER N-(4-NITROBENZOYL)-L-GLUTAMIC ACID DIETHYL ESTER 7148-24-5 C16H20N2O7
BENZOYL-D-PHE-OH BENZOYL-D-PHE-OH 37002-52-1 C16H15NO3
D-THREONINE BENZYL ESTER HYDROCHLORIDE D-THREONINE BENZYL ESTER HYDROCHLORIDE 75748-36-6 C11H16ClNO3
Z-DEHYDRO-ALA-OH Z-DEHYDRO-ALA-OH 39692-63-2 C11H11NO4
GLYCYL-DL-METHIONINE GLYCYL-DL-METHIONINE 1999-34-4 C7H14N2O3S
(S)-(-)-2-AMINO-1,1,2-TRIPHENYLETHANOL (S)-(-)-2-AMINO-1,1,2-TRIPHENYLETHANOL 129704-13-8 C20H19NO
Ethyl 2-(acetylamino)-3-[3,5-diamino-4-(4-methoxyphenoxy)phenyl]propanoate Ethyl 2-(acetylamino)-3-[3,5-diamino-4-(4-methoxyphenoxy)phenyl]propanoate 440667-78-7 C20H25N3O5
H-LYS(ME3)-OH HCL H-LYS(ME3)-OH HCL 201009-98-5 C9H21ClN2O2
5-AMINO-PYRIMIDINE-2-CARBOXYLIC ACID 5-AMINO-PYRIMIDINE-2-CARBOXYLIC ACID 56621-98-8 C5H5N3O2
BENZOYL-FVR-PNA BENZOYL-FVR-PNA 54799-93-8 C33H40N8O6
N-BENZYL-L-SERINE, METHYL ESTER N-BENZYL-L-SERINE, METHYL ESTER 123639-56-5 C11H15NO3
L-HOMOGLUTAMINE L-HOMOGLUTAMINE 5632-90-6 C6H12N2O3
EC EC 14344-48-0 C8H16N2O4S2
BIS-TYRPHOSTIN BIS-TYRPHOSTIN C23H20N4O6
N-Methyl-D-glutamic acid N-Methyl-D-glutamic acid 77481-28-8 C6H11NO4
L-Alanylglycine methyl ester L-Alanylglycine methyl ester 51513-59-8 C6H12N2O3
L-Alanyl-L-alanine L-Alanyl-L-alanine 2392-61-2 C6H12N2O3
BOC-GLU-NH2 BOC-GLU-NH2 18800-74-3 C10H18N2O5
N-ME-DL-VAL-OH HCL N-ME-DL-VAL-OH HCL 2566-32-7 C6H13NO2
Z-SAR-OH Z-SAR-OH 39608-31-6 C11H13NO4
trans-4-(tert-Butyldiphenylsilyloxy)-L-proline trans-4-(tert-Butyldiphenylsilyloxy)-L-proline 259212-61-8 C21H27NO3Si
Boc-D-Homoserine Boc-D-Homoserine 67198-87-2 C9H18NNaO5
N-ALPHA-METHYL-D-ALANINE HYDROCHLORIDE N-ALPHA-METHYL-D-ALANINE HYDROCHLORIDE C4H10ClNO2
FMOC-3-(1-PYRENYL)-L-ALANINE FMOC-3-(1-PYRENYL)-L-ALANINE 183071-07-0 C34H25NO4
2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-PHENYL-PROPIONIC ACID 2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-PHENYL-PROPIONIC ACID 100750-05-8 C24H21NO4
AC-ALA-OME AC-ALA-OME 3619-02-1 C6H11NO3
DL-2-AMINO-1-HEXANOL DL-2-AMINO-1-HEXANOL 5665-74-7 C6H15NO
FMOC-D-2-AMINO-5-PHENYL-PENTANOIC ACID FMOC-D-2-AMINO-5-PHENYL-PENTANOIC ACID 1217731-48-0 C26H25NO4
BOC-(R)-3-THIENYLGLYCINE BOC-(R)-3-THIENYLGLYCINE 33130-97-1 C11H15NO4S
3-FLUORO-4-METHYL-DL-PHENYLGLYCINE 3-FLUORO-4-METHYL-DL-PHENYLGLYCINE 261951-76-2 C9H10FNO2
N,O-DI(2,4-DNP)-L-TYROSINE N,O-DI(2,4-DNP)-L-TYROSINE 1694-93-5 C21H15N5O11
H-ALA-PRO-OME HCL H-ALA-PRO-OME HCL 71067-42-0 C9H17ClN2O3
5-NITRO-DL-TRYPTOPHAN 5-NITRO-DL-TRYPTOPHAN 6525-46-8 C11H11N3O4
H-D-LEU-LEU-OH H-D-LEU-LEU-OH 38689-31-5 C12H24N2O3
TYRPHOSTIN A63 TYRPHOSTIN A63 5553-97-9 C10H8N2O
BZ-TRP-OH BZ-TRP-OH 4302-66-3 C18H16N2O3
N N-DIMETHYLAMINOACETIC ACID SODIUM SALT N N-DIMETHYLAMINOACETIC ACID SODIUM SALT 18319-88-5 C4H10NNaO2
AC-PHE-LYS-OH AC-PHE-LYS-OH 14287-21-9 C17H25N3O4
N-NITROSO-L-PROLINE N-NITROSO-L-PROLINE 7519-36-0 C5H8N2O3
GLY-PRO 4-METHOXY-BETA-NAPHTHYLAMIDE HYDROCHLORIDE GLY-PRO 4-METHOXY-BETA-NAPHTHYLAMIDE HYDROCHLORIDE 100929-90-6 C18H22ClN3O3
N-Dodecanoyl-L-alanine N-Dodecanoyl-L-alanine 775242-37-0 C15H29NO3
1-(1-Oxohexadecyl)-L-proline 1-(1-Oxohexadecyl)-L-proline 59441-32-6 C21H39NO3
Z-IETD-AFC Z-IETD-AFC 219138-02-0 C37H42F3N5O13
POLY-L-ARGININE HYDROCHLORIDE POLY-L-ARGININE HYDROCHLORIDE 26982-20-7 C6H14N4O2
TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER 120806-96-4 C13H15NO4
4-AMINOBUTYLPHOSPHONIC ACID 4-AMINOBUTYLPHOSPHONIC ACID 35622-27-6 C4H12NO3P
BOC-L-TYROSINE ETHYL ESTER BOC-L-TYROSINE ETHYL ESTER 72594-77-5 C16H23NO5
(+)-N-BENZOYLGLUTAMIC ACID (+)-N-BENZOYLGLUTAMIC ACID 58094-18-1 C12H13NO5
Alanosine Alanosine 5854-93-3 C3H7N3O4
Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate 810670-03-2 C12H14ClNO3
Ethylenediamine-N,N'-bis((2-hydroxyphenyl)acetic acid) Ethylenediamine-N,N'-bis((2-hydroxyphenyl)acetic acid) 1170-02-1 C18H20N2O6
Boc-L-3-Bromophenylalanine Boc-L-3-Bromophenylalanine 82278-95-3 C14H18BrNO4
(2S)-2,6-DIAMINO-N-[(1S)-1-METHYL-2-PHENYLETHYL]HEXANAMIDE DIMETHANESULFONATE (2S)-2,6-DIAMINO-N-[(1S)-1-METHYL-2-PHENYLETHYL]HEXANAMIDE DIMETHANESULFONATE 608137-33-3 C16H29N3O4S
S-Butyl-D-cysteine S-Butyl-D-cysteine 4134-56-9 C7H15NO2S
3-(N,N-Diethylamino)-L-alanine 3-(N,N-Diethylamino)-L-alanine 754167-24-3 C7H16N2O2
H-D-ALA-PNA HCL H-D-ALA-PNA HCL C9H12ClN3O3
D-Proline, 1-glycyl- (9CI) D-Proline, 1-glycyl- (9CI) 71884-56-5 C7H12N2O3
Benzoic acid, 3-acetyl-4-amino-, methyl ester (9CI) Benzoic acid, 3-acetyl-4-amino-, methyl ester (9CI) 111714-47-7 C10H11NO3
Pyrazinecarboxylic acid, 6-amino- (9CI) Pyrazinecarboxylic acid, 6-amino- (9CI) 61442-38-4 C5H5N3O2
3-(Dimethylamino)propanoicacid 3-(Dimethylamino)propanoicacid 6300-04-5 C5H11NO2
N-Boc-1-phenylmethyl-D-histidine N-Boc-1-phenylmethyl-D-histidine 65717-64-8 C18H23N3O4
(R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL
(R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL 158807-47-7 C14H21NO3
1-N-CBZ-4-HYDROXY-BETA-PROLINE
1-N-CBZ-4-HYDROXY-BETA-PROLINE 886362-64-7 C13H15NO5
(R)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID C9H10BrNO2
H-THR-OBZL OXALATE (1:1) H-THR-OBZL OXALATE (1:1) 201274-07-9 C13H17NO7
DL-Glutamine DL-Glutamine 6899-04-3 C5H10N2O3
3-hydroxyglutamic acid 3-hydroxyglutamic acid 533-62-0 C5H9NO5
3-[[(1,1-Dimethylethoxy)carbonyl]amino]-L-alanine methyl ester 3-[[(1,1-Dimethylethoxy)carbonyl]amino]-L-alanine methyl ester 77087-60-6 C9H18N2O4
3-(N,N-Diethanolamino)-L-alanine 3-(N,N-Diethanolamino)-L-alanine 700801-50-9 C7H16N2O4
Boc-L-glutamic acid γ-allyl ester Boc-L-glutamic acid γ-allyl ester 132286-79-4 C13H21NO6
Fmoc-L-allo-isoleucine Fmoc-L-allo-isoleucine 251316-98-0 C21H23NO4
N-BOC-(S)-2-AMINO-1-BUTANOL, 96% N-BOC-(S)-2-AMINO-1-BUTANOL, 96% 150736-72-4 C9H19NO3
3-Imidazolyl-L-alanine 3-Imidazolyl-L-alanine 114717-14-5 C6H9N3O2
3-(N,N-Dimethylamino)-D-alanine 3-(N,N-Dimethylamino)-D-alanine 206559-98-0 C5H12N2O2
BETA-(1,2,4-TRIAZOL-3-YL)-DL-ALANINE BETA-(1,2,4-TRIAZOL-3-YL)-DL-ALANINE 3184-54-1 C5H8N4O2
FMOC-(S)-3-AMINO-3-(4-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(4-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 507472-21-1 C25H20F3NO4
3-(4-Pyridyl)-DL-alanine 3-(4-Pyridyl)-DL-alanine 1956-21-4 C8H10N2O2
S-Trityl-D-cysteine S-Trityl-D-cysteine 25840-82-8 C22H21NO2S
(S)-3-TERT-BUTYL-BETA-ALANINE
(S)-3-TERT-BUTYL-BETA-ALANINE 367278-48-6 C7H15NO2
3-CHLORO-DL-PHENYLALANINE 3-CHLORO-DL-PHENYLALANINE 1956-15-6 C9H10ClNO2
H-GLY-PRO-AMC HBR H-GLY-PRO-AMC HBR 115035-46-6 C17H20BrN3O4
FMOC-4-AZIDO-L-PHENYLALANINE FMOC-4-AZIDO-L-PHENYLALANINE 163217-43-4 C24H20N4O4
L-Pyroglutamamide L-Pyroglutamamide 16395-57-6 C5H8N2O2
1H-Pyrazole-3-carboxylicacid,4-amino-1-phenyl-(9CI) 1H-Pyrazole-3-carboxylicacid,4-amino-1-phenyl-(9CI) 64299-26-9 C10H9N3O2
[(1,1-DIOXO-TETRAHYDRO-1LAMBDA6-THIOPHEN-3-YL)-METHYL-AMINO]-ACETIC ACID [(1,1-DIOXO-TETRAHYDRO-1LAMBDA6-THIOPHEN-3-YL)-METHYL-AMINO]-ACETIC ACID 51070-58-7 C7H13NO4S
N-ME-SER(TBU)-OH N-ME-SER(TBU)-OH 197632-83-0 C8H17NO3
N-(tert-buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine N-(tert-buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine 30033-24-0 C14H19NO6
FMOC-ORN(ALOC)-OH FMOC-ORN(ALOC)-OH 147290-11-7 C24H26N2O6
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