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
FMOC-D-LYS(MTT)-OH FMOC-D-LYS(MTT)-OH 198544-94-4 C41H40N2O4
4-Amino-1H-imidazole-2-carboxylic acid 4-Amino-1H-imidazole-2-carboxylic acid 155815-92-2 C4H5N3O2
4-AMINOQUINOLINE-2-CARBOXYLIC ACID 4-AMINOQUINOLINE-2-CARBOXYLIC ACID 157915-66-7 C10H8N2O2
(+)-(1S,3R)-N-FMOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID (+)-(1S,3R)-N-FMOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID 220497-66-5 C21H21NO4
L-Leucinamide hydrochloride L-Leucinamide hydrochloride 10466-61-2 C6H15ClN2O
(R)-alpha,alpha-Diphenylmethylprolinol (R)-alpha,alpha-Diphenylmethylprolinol 144119-12-0 C18H21NO
(R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid (R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid 135270-40-5 C11H12ClNO3
4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE 3223-07-2 C13H19Cl3N2O2
DL-THREONINE METHYL ESTER HYDROCHLORIDE DL-THREONINE METHYL ESTER HYDROCHLORIDE 62076-66-8 C5H12ClNO3
DL-3,4-Dimethylphenylalanine DL-3,4-Dimethylphenylalanine 103957-56-8 C11H15NO2
3,5-Difluoro-D-phenylalanine 3,5-Difluoro-D-phenylalanine 266360-63-8 C9H9F2NO2
H-CYS(ACM)-OH HCL H-CYS(ACM)-OH HCL 28798-28-9 C6H13ClN2O3S
BZ-THR-OME BZ-THR-OME 79893-89-3 C12H15NO4
PTH-L-PROLINE PTH-L-PROLINE 4333-21-5 C12H12N2OS
ETHYL 2-AMINO-2-PHENYLACETATE HYDROCHLORIDE ETHYL 2-AMINO-2-PHENYLACETATE HYDROCHLORIDE 879-48-1 C10H14ClNO2
(2R)-2-Aminopropanamide hydrochloride (2R)-2-Aminopropanamide hydrochloride 71810-97-4 C3H9ClN2O
BOC-ALA-OBZL BOC-ALA-OBZL 51814-54-1 C15H21NO4
N-2-NITROPHENYLSULFENYL-L-LEUCINE N-2-NITROPHENYLSULFENYL-L-LEUCINE 7685-67-8 C12H16N2O4S
N-BENZOYL-DL-PHENYLALANINE 2-NAPHTHYL ESTER N-BENZOYL-DL-PHENYLALANINE 2-NAPHTHYL ESTER 2134-24-9 C26H21NO3
FMOC-(R)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRIC ACID 331763-63-4 C25H22FNO4
BOC-LEU-OME BOC-LEU-OME 63096-02-6 C12H23NO4
N-Fmoc-N-methyl-O-benzyl-L-serine N-Fmoc-N-methyl-O-benzyl-L-serine 84000-14-6 C26H25NO5
BOC-(R)-3-AMINO-4-(2-THIENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-THIENYL)-BUTYRIC ACID 269726-89-8 C13H19NO4S
GLYCYL-DL-ASPARAGINE GLYCYL-DL-ASPARAGINE 32729-21-8 C6H11N3O4
AC-TYR(AC)-OH AC-TYR(AC)-OH 17355-23-6 C13H15NO5
(S)-3-AMINO-5-HEXENOIC ACID HYDROCHLORIDE (S)-3-AMINO-5-HEXENOIC ACID HYDROCHLORIDE 270263-02-0 C6H11NO2
L-ARGININE 7-AMIDO-4-METHYLCOUMARIN DIHYDROCHLORIDE L-ARGININE 7-AMIDO-4-METHYLCOUMARIN DIHYDROCHLORIDE 113712-08-6 C16H23Cl2N5O3
DL-ALANYL-DL-ASPARAGINE DL-ALANYL-DL-ASPARAGINE 1999-41-3 C7H13N3O4
DL-BETA-HYDROXYNORVALINE DL-BETA-HYDROXYNORVALINE 34042-00-7 C5H11NO3
H-3,5-DIBROMO-D-TYR-OH H-3,5-DIBROMO-D-TYR-OH 50299-42-8 C9H9Br2NO3
H-GLU-PNA H-GLU-PNA 24032-35-7 C11H13N3O5
BOC-VAL-OME BOC-VAL-OME 58561-04-9 C11H21NO4
(S)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID HCL (S)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID HCL 403661-76-7 C10H13BrClNO2
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-1-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-1-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID 195387-29-2 C21H18N2O4
N-Methyl-L-leucine N-Methyl-L-leucine 3060-46-6 C7H15NO2
Z-TYR-ONP Z-TYR-ONP 3556-56-7 C23H20N2O7
N-[4-(TRIFLUOROMETHYL)BENZOYL]-L-METHIONINE METHYL ESTER N-[4-(TRIFLUOROMETHYL)BENZOYL]-L-METHIONINE METHYL ESTER 175202-25-2 C14H16F3NO3S
AC-DL-PHE-OH AC-DL-PHE-OH 2901-61-3 C11H13NO3
(R)-(+)-2-AMINO-3-METHYL-1,1-DIPHENYL-1-BUTANOL (R)-(+)-2-AMINO-3-METHYL-1,1-DIPHENYL-1-BUTANOL 86695-06-9 C17H21NO
FMOC-L-BETA-HOMOTRYPTOPHAN FMOC-L-BETA-HOMOTRYPTOPHAN 353245-98-4 C27H24N2O4
SUC-ALA-ALA-PRO-PHE-PNA SUC-ALA-ALA-PRO-PHE-PNA 70967-97-4 C30H36N6O9
Transglutaminase Transglutaminase 80146-85-6 C27H44O3H2O
BOC-ORN(2-CL-Z)-OH BOC-ORN(2-CL-Z)-OH 118554-00-0 C18H25ClN2O6
NALPHA-(TERT-BUTOXYCARBONYL)-L-ARGININE 4-NITROANILIDE HYDROCHLORIDE NALPHA-(TERT-BUTOXYCARBONYL)-L-ARGININE 4-NITROANILIDE HYDROCHLORIDE 99306-64-6 C17H27ClN6O5
N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol 2212-32-0 C7H18N2O
O-ACETYL-L-TYROSINE O-ACETYL-L-TYROSINE 6636-22-2 C11H13NO4
2-AMINO-3,3-DIPHENYL-PROPIONIC ACID 2-AMINO-3,3-DIPHENYL-PROPIONIC ACID 62653-26-3 C15H15NO2
Z-ARG-OH HCL Z-ARG-OH HCL 73496-41-0 C14H21ClN4O4
2-AMINO-2-(2-HYDROXYPHENYL)ACETIC ACID 2-AMINO-2-(2-HYDROXYPHENYL)ACETIC ACID 25178-38-5 C8H9NO3
(+/-)-NICOTINE-METHYL-D3 (+/-)-NICOTINE-METHYL-D3 69980-24-1 C10H11D3N2
3-Iodo-L-tyrosine methyl ester 3-Iodo-L-tyrosine methyl ester 70277-02-0 C10H12INO3
H-ARG(OH)-OH ACOH H-ARG(OH)-OH ACOH 53598-01-9 C8H18N4O5
(1S,2S)-trans-2-Aminocyclopentanol hydrochloride (1S,2S)-trans-2-Aminocyclopentanol hydrochloride 68327-04-8 C5H12ClNO
(R)-4-CHLORO PHENYLGLYCINE (R)-4-CHLORO PHENYLGLYCINE 43189-37-3 C8H8ClNO2
4-Amino-L-phenylalanine hydrochloride 4-Amino-L-phenylalanine hydrochloride 62040-55-5 C9H13ClN2O2
PYRIDOXYLIDENE-L-GLUTAMIC ACID DIPOTASSIUM SALT PYRIDOXYLIDENE-L-GLUTAMIC ACID DIPOTASSIUM SALT 13934-03-7 C13H16N2O6
FMOC-ASP(ODMAB)-OH FMOC-ASP(ODMAB)-OH 269066-08-2 C39H42N2O8
BOC-(R)-3-AMINO-3-(2,3-DICHLORO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(2,3-DICHLORO-PHENYL)-PROPIONIC ACID 500788-91-0 C14H17Cl2NO4
4-ACETAMIDO-2-METHYLBENZOIC ACID 4-ACETAMIDO-2-METHYLBENZOIC ACID 103204-69-9 C10H11NO3
AC-VEID-AMC AC-VEID-AMC 219137-97-0 C32H43N5O11
BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER 203866-18-6 C11H18FNO4
(R)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID 151911-22-7 C9H10FNO2
Magnesium aspartate tetrahydrate Magnesium aspartate tetrahydrate 7018-07-7 C4H13MgNO8
METHYL 2-AMINO-3-MERCAPTOPROPANOATE HYDROCHLORIDE METHYL 2-AMINO-3-MERCAPTOPROPANOATE HYDROCHLORIDE 70361-61-4 C4H10ClNO2S
Boc-Glycine hydrazide Boc-Glycine hydrazide 6926-09-6 C7H15N3O3
N-FORMYL-DL-ALANINE N-FORMYL-DL-ALANINE 5893-10-7 C4H7NO3
N-(3-Indolylacetyl)-L-valine N-(3-Indolylacetyl)-L-valine 57105-42-7 C15H18N2O3
FMOC-(R)-3-AMINO-3-(3-BROMO-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(3-BROMO-PHENYL)-PROPIONIC ACID 517905-85-0 C24H20BrNO4
H-LYS(TOS)-OH H-LYS(TOS)-OH 2130-76-9 C13H20N2O4S
Sodium 1-palmitoyl-L-prolinate Sodium 1-palmitoyl-L-prolinate 58725-33-0 C21H38NNaO3
FMOC-(R)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID 511272-32-5 C25H23NO5
H-D-PRO-OET HCL H-D-PRO-OET HCL 131477-20-8 C7H14ClNO2
(R)-3-AMINO-3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 793663-51-1 C10H10F3NO2
N-ALPHA-BOC-(+/-)-2,3-DIAMINOPROPIONIC ACID N-ALPHA-BOC-(+/-)-2,3-DIAMINOPROPIONIC ACID 159002-17-2 C8H16N2O4
(R)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 331763-62-3 C10H13ClFNO2
Z-GLY-GLY-OET Z-GLY-GLY-OET 1145-81-9 C12H15NO4
SUC-LEU-TYR-AMC SUC-LEU-TYR-AMC 94367-20-1 C29H33N3O8
N-tert-Butyloxycarbonyl-N-methyl-O-benzyl-L-threonine N-tert-Butyloxycarbonyl-N-methyl-O-benzyl-L-threonine 64263-80-5 C17H25NO5
PYR-ALA-OH PYR-ALA-OH 21282-08-6 C8H12N2O4
N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER N-ACETYL-S-BENZYL-L-CYSTEINE METHYL ESTER 77549-14-5 C13H17NO3S
FMOC-ARG(MTS)-OH FMOC-ARG(MTS)-OH 88743-97-9 C30H34N4O6S
H-D-LEU-OTBU HCL H-D-LEU-OTBU HCL 67617-35-0 C10H21NO2
(RS)-4-CARBOXY-3-HYDROXYPHENYLGLYCINE (RS)-4-CARBOXY-3-HYDROXYPHENYLGLYCINE 134052-66-7 C9H9NO5
L-PHENYLALANINE DEHYDROGENASE L-PHENYLALANINE DEHYDROGENASE 69403-12-9
Bromomethyl methyl ether Bromomethyl methyl ether 13057-17-5 C2H5BrO
AC-SER(TBU)-OH AC-SER(TBU)-OH 77285-09-7 C9H17NO4
(S)-2-Acetamido-3-(4-nitrophenyl)propanoic acid (S)-2-Acetamido-3-(4-nitrophenyl)propanoic acid 17363-92-7 C11H12N2O5
Methyl (S)-3-acetamido-3-(4-methoxyphenyl)propanoate Methyl (S)-3-acetamido-3-(4-methoxyphenyl)propanoate 434957-82-1 C13H17NO4
Fmoc-L-Dapa-OH Fmoc-L-Dapa-OH 181954-34-7 C18H18N2O4
Fmoc-Asp-OFm Fmoc-Asp-OFm 187671-16-5 C33H27NO6
H-D-Val-OtBu.HCl H-D-Val-OtBu.HCl 104944-18-5 C9H20ClNO2
DL-α,α'-diaminosuccinic acid DL-α,α'-diaminosuccinic acid 29276-73-1 C4H8N2O4
Fmoc-beta-(R)-4-methoxyphenylalanine Fmoc-beta-(R)-4-methoxyphenylalanine 511272-33-6 C25H23NO5
(2R,3S)-3-phenylisoserine methyl ester (2R,3S)-3-phenylisoserine methyl ester 131968-74-6 C10H13NO3
(S)-2-Amino-2-methyl-4-pentenoic acid (S)-2-Amino-2-methyl-4-pentenoic acid 96886-56-5 C6H11NO2
2-Hydroxy-D-phenylalanine 2-Hydroxy-D-phenylalanine 24008-77-3 C9H11NO3
2,3-Difluoro-D-phenylalanine 2,3-Difluoro-D-phenylalanine 266360-59-2 C9H9F2NO2
L-2-Thiolhistidine L-2-Thiolhistidine C6H9N3O2S
Thr(tBu)-OtBu Thr(tBu)-OtBu C12H25NO3
D-Cyclobutylalanine D-Cyclobutylalanine 174266-00-3 C7H13NO2
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