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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
GLYCINE-2,2-D2 GLYCINE-2,2-D2 4896-75-7 C2H3D2NO2
(R)-3-Trifluoromethyl-homophenylalanine (R)-3-Trifluoromethyl-homophenylalanine 1260586-95-5 C11H12F3NO2
Phenylalanine hydroxylase (PAH) recombinant protein Phenylalanine hydroxylase (PAH) recombinant protein
Fmoc-Gln(Trt)-Gly-OH Fmoc-Gln(Trt)-Gly-OH
FMOC-4-AMINOMETHYL-PHENYLACETIC ACID FMOC-4-AMINOMETHYL-PHENYLACETIC ACID 176504-01-1 C24H21NO4
Z-ARG(MBS)-OH DCHA Z-ARG(MBS)-OH DCHA 58810-11-0 C33H49N5O7S
ALOC-D-PHE-OH DCHA ALOC-D-PHE-OH DCHA 152507-71-6 C13H15NO4
TOS-GLY-OSU TOS-GLY-OSU 68385-26-2 C13H14N2O6S
diaquatetrachloro[mu-[N-ethyl-N-[(tridecafluorohexyl)sulphonyl]glycinato-O1:O1']]-mu-hydroxybis(propan-2-ol)dichromium diaquatetrachloro[mu-[N-ethyl-N-[(tridecafluorohexyl)sulphonyl]glycinato-O1:O1']]-mu-hydroxybis(propan-2-ol)dichromium 68891-98-5 C16H23Cl4Cr2F13NO9S
Fmoc-His-Aib-OH Fmoc-His-Aib-OH 1446013-07-5 C25 H26 N4 O5
Boc-Tyr(tBu)-Aib-Glu(OtBu)-Gly-OH Boc-Tyr(tBu)-Aib-Glu(OtBu)-Gly-OH 2682040-93-1
Fmoc-2-Methoxy-D-Phenylalanine Fmoc-2-Methoxy-D-Phenylalanine 170642-30-5 C25H23NO5
DL-2,5-Dimethylphenylalanine DL-2,5-Dimethylphenylalanine 103854-25-7 C11H15NO2
HATU HATU 148893-10-1 C10H15F6N6OP
L-citrulline hydrochloride L-citrulline hydrochloride 197704-69-1 C6H14ClN3O3
Ethanaminium, 2-carboxy-N,N,N-trimethyl-2-[[(9Z,12Z)-1-oxo-9,12-octadecadien-1-yl]oxy]-, inner salt, (2S)- Ethanaminium, 2-carboxy-N,N,N-trimethyl-2-[[(9Z,12Z)-1-oxo-9,12-octadecadien-1-yl]oxy]-, inner salt, (2S)- 38179-45-2 C24H43NO4
2,5-Piperazinedione, 3-benzyl-6-isopropyl- 2,5-Piperazinedione, 3-benzyl-6-isopropyl- 14474-71-6 C14H18N2O2
tBuO-C20-Glu(AEEA-AEEA-OSu)-OtBu tBuO-C20-Glu(AEEA-AEEA-OSu)-OtBu 1118767-17-1 C49H86N4O15
copper(2+) bis(aminoacetate) copper(2+) bis(aminoacetate)
Fmoc-Lys[γ-Glu(OtBu)-C18-OtBu)]-OH Fmoc-Lys[γ-Glu(OtBu)-C18-OtBu)]-OH 1931109-48-6
H-DL-Phe-NH2 H-DL-Phe-NH2 17193-31-6 C9H12N2O
FMOC-L-3,5-DIFLUOROPHE FMOC-L-3,5-DIFLUOROPHE 205526-24-5 C24H19F2NO4
H-D-BPA-OH H-D-BPA-OH 201466-03-7 C16H15NO3
Glutamic acid Glutamic acid 6899-05-4 C5H9NO4
3-METHOXY-L-PHENYLALANINE 3-METHOXY-L-PHENYLALANINE 33879-32-2 C10H13NO3
NAGLY NAGLY 179113-91-8 C22H35NO3
Fmoc-Ala-N-Me-Ile-OH Fmoc-Ala-N-Me-Ile-OH
AC-LEU-PNA AC-LEU-PNA 19746-40-8 C14H19N3O4
BOC-TYR-D-ALA-GLY-OH BOC-TYR-D-ALA-GLY-OH 64410-47-5 C19H27N3O7
Fmoc-Glu(OtBu)-α-Me-Phe-OH Fmoc-Glu(OtBu)-α-Me-Phe-OH
(R)-2-amino-2-methyl-hept-6-enoic acid (R)-2-amino-2-methyl-hept-6-enoic acid 1196090-89-7 C8H15NO2
1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester 170908-81-3 C20H31N5O10
(S)-N-FMoc-2-(5'-pentenyl)alanine (S)-N-FMoc-2-(5'-pentenyl)alanine 288617-74-3 C24H27NO4
4-Ethynyl-L-phenylalanine HCl 4-Ethynyl-L-phenylalanine HCl 278605-15-5 C11H11NO2
L-Phenylalanine-13C9,15N
		
	L-Phenylalanine-13C9,15N 878339-23-2 C9H11NO2
3-IODO-DL-PHENYLALANINE 3-IODO-DL-PHENYLALANINE 20846-38-2 C9H10INO2
CYSTEAMINE S-PHOSPHATE SODIUM SALT CYSTEAMINE S-PHOSPHATE SODIUM SALT 3724-89-8 C2H9NNaO3PS
2-(TRIFLUOROMETHYL)-DL-PHENYLALANINE 2-(TRIFLUOROMETHYL)-DL-PHENYLALANINE 119009-47-1 C10H10F3NO2
Z-GLU-PHE-OH Z-GLU-PHE-OH 987-84-8 C22H24N2O7
Fmoc-AEEA-AEEA Fmoc-AEEA-AEEA 560088-89-3 C27H34N2O9
Fmoc-N-Me-D-HomoPhe-OH Fmoc-N-Me-D-HomoPhe-OH
Fmoc-α-methyl-D-4-fluorophenylalanine Fmoc-α-methyl-D-4-fluorophenylalanine 1217777-84-8 C25H22FNO4
tetramethylammomium glycinate tetramethylammomium glycinate 55378-67-1 C6H16N2O2
AC-MET(O)-OH AC-MET(O)-OH 108646-71-5 C7H13NO4S
4-aminomethylphenylalanine 4-aminomethylphenylalanine 1991-96-4 C10H14N2O2
Fmoc-L-Lys[C20-OtBu-Glu(OtBu)-AEEA]-OH Fmoc-L-Lys[C20-OtBu-Glu(OtBu)-AEEA]-OH 2612237-97-3
Z-PHE-GLY-GLY-OH Z-PHE-GLY-GLY-OH 37700-64-4 C21H23N3O6
Fmoc-Leu-Pro-Pro-OH Fmoc-Leu-Pro-Pro-OH
N-(1-Oxohexadecyl)-L-glutaMic Acid tert-Butyl Ester N-(1-Oxohexadecyl)-L-glutaMic Acid tert-Butyl Ester 536721-25-2 C25H47NO5
4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine 4-[(AMinocarbonyl)aMino]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-D-phenylalanine 324017-22-3 C25H23N3O5
4-Azido-L-phenylalanine (hydrochloride) 4-Azido-L-phenylalanine (hydrochloride) 34670-43-4 C9H11ClN4O2
Boc-L-vinylglycine Boc-L-vinylglycine 91028-39-6 C9H15NO4
Fmoc-Glu(OtBu)-Gly-OH Fmoc-Glu(OtBu)-Gly-OH 866044-63-5 C26H30N2O7
(D-TYR1,N-ME-PHE3)-NEUROPEPTIDE FF (D-TYR1,N-ME-PHE3)-NEUROPEPTIDE FF 145274-93-7 C55H78N14O11
D-2,4-DIMETHYLPHE D-2,4-DIMETHYLPHE 465500-97-4 C11H15NO2
2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid 1068435-19-7 C27H31NO4
Fmoc-Thr(OtBu)-α-Me-Phe-OH Fmoc-Thr(OtBu)-α-Me-Phe-OH
Fmoc-Tyr(Me)-α-Me-Pro-OH Fmoc-Tyr(Me)-α-Me-Pro-OH
(S)-N-Fmoc-2-(3'-butenyl)alanine (S)-N-Fmoc-2-(3'-butenyl)alanine 288617-72-1 C22H23NO4
(2-BroMo-phenylaMino)-acetic acid (2-BroMo-phenylaMino)-acetic acid 40789-38-6 C8H8BrNO2
FMOC-D-2-AMINOMETHYLPHE(BOC) FMOC-D-2-AMINOMETHYLPHE(BOC) 1217729-44-6 C30H32N2O6
FMoc-N-Me-D-Asn-OH FMoc-N-Me-D-Asn-OH 2044709-67-1 C20H20N2O5
Fmoc-4-trifluoromethyl-L-homophenylalanine Fmoc-4-trifluoromethyl-L-homophenylalanine 1260591-49-8 C26H22F3NO4
BOC-GLY-GLY-GLY-OH BOC-GLY-GLY-GLY-OH 28320-73-2 C11H19N3O6
Phosphatidylserine PEG Maleimide, PS PEG Mal Phosphatidylserine PEG Maleimide, PS PEG Mal
2-fluoro-N-[(phenylmethoxy)carbonyl]- D-Phenylalanine 2-fluoro-N-[(phenylmethoxy)carbonyl]- D-Phenylalanine 7557-34-8 C17H16FNO4
Boc-3-trifluoromethyl-D-homophenylalanine Boc-3-trifluoromethyl-D-homophenylalanine 1260589-08-9 C16H20F3NO4
DL-Pipecolinic acid DL-Pipecolinic acid 4043-87-2 C6H11NO2
AC-GLY-ONP AC-GLY-ONP 3304-61-8 C10H10N2O5
L-ISOLEUCINE (U-13C6,15N) L-ISOLEUCINE (U-13C6,15N) 202468-35-7 C6H13NO2
L-3-THIENYLALANINE L-3-THIENYLALANINE 3685-51-6 C7H9NO2S
FMOC-L-7-AZATRP FMOC-L-7-AZATRP 737007-45-3 C25H21N3O4
Tirzepatide Tirzepatide 2023788-19-2 C225H348N48O68
Boc-Tyr(tBu)-Aib-OH Boc-Tyr(tBu)-Aib-OH
2-CHLORO-N-(2-METHYLPHENYL)PROPANAMIDE 2-CHLORO-N-(2-METHYLPHENYL)PROPANAMIDE 19281-31-3 C10H12ClNO
Fmoc-2,4-difluoro-D-homophenylalanine Fmoc-2,4-difluoro-D-homophenylalanine 1260601-13-5 C25H21F2NO4
Phenylalanine, N-acetyl-, monosodium salt (9CI) Phenylalanine, N-acetyl-, monosodium salt (9CI) 74407-30-0 C11H12NNaO3
H-DL-PHE-OTBU HCL H-DL-PHE-OTBU HCL 75898-47-4 C13H20ClNO2
N-(PHENYLACETYL)-L-PHENYLALANINE N-(PHENYLACETYL)-L-PHENYLALANINE 738-75-0 C17H17NO3
BOC-ASP(OBZL)-PHE-OH BOC-ASP(OBZL)-PHE-OH 68763-45-1 C25H30N2O7
L-PHENYLALANINE (1-13C) L-PHENYLALANINE (1-13C) 81201-86-7 C9H11NO2
(R)-4-methoxyphenylglycine (R)-4-methoxyphenylglycine 24593-49-5 C9H11NO3
2,6-Dichloro-D-Phenylalanine 2,6-Dichloro-D-Phenylalanine 1241684-03-6 C9H9Cl2NO2
Fmoc-D-phenylglycine(4-OtBu) Fmoc-D-phenylglycine(4-OtBu) 1270295-28-7 C27H27NO5
Z-D-PHE-ONP Z-D-PHE-ONP 2578-85-0 C23H20N2O6
2-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID 2-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID 7635-28-1 C10H13NO3
L-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5,7-dimethyl- L-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5,7-dimethyl- 643024-95-7 C28H26N2O4
Fmoc-Glu(OtBu)-Val-OH Fmoc-Glu(OtBu)-Val-OH 2897581-02-9 C29H36N2O7
DL-PHENYLALANINE-15N DL-PHENYLALANINE-15N 81387-53-3 C9H11NO2
L-4-AMINOMETHYLPHE L-4-AMINOMETHYLPHE 150338-20-8 C10H14N2O2
BOC-DL-ILE-OH BOC-DL-ILE-OH 116194-21-9 C11H21NO4
N-alpha-Fmoc-N-epsilon-4-methoxytrityl-L-lysine N-alpha-Fmoc-N-epsilon-4-methoxytrityl-L-lysine 159857-60-0 C41H40N2O5
(2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine 109384-24-9 C10H18N2O4
(S)-2-amino-2-methyl-4-pentenoicacid (S)-2-amino-2-methyl-4-pentenoicacid 1011309-61-7 C8H15NO2
GlucosaMine L-5-Methyltetrahydrofolate GlucosaMine L-5-Methyltetrahydrofolate 1181972-37-1 C26H38N8O11
N-[N′-FMoc-(2′-aMinoethyl)]glycine N-[N′-FMoc-(2′-aMinoethyl)]glycine 172405-45-7 C19H20N2O4
(R)- 2-(3'-butenyl) glycine (R)- 2-(3'-butenyl) glycine 103067-78-3 C6H11NO2
α-Me-Phe(4-OCF<sub>3<sub>)-OH α-Me-Phe(4-OCF3)-OH 1269926-90-0 C11H12F3NO3
methyl (R)-2-amino-3-(4-bromophenyl)propanoate hydrochloride methyl (R)-2-amino-3-(4-bromophenyl)propanoate hydrochloride 459133-43-8 C10H13BrClNO2
N-Boc-4-fluoro-(R)-homophenylalanine N-Boc-4-fluoro-(R)-homophenylalanine 1217624-82-2 C15H20FNO4
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