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甘氨酸类衍生物

学名为氨基乙酸,是结构最简单且唯一没有旋光异构体的α-氨基酸。1820年,化学家布拉孔诺通过用盐酸处理明胶获得一种具有甜味的物质,最初误认为是糖类化合物,经分析发现它是一种含氮并带有羧基的化合物,可用于制造氨气,并将其命名为甘氨酸。

甘氨酸常以四边柱状、无色单斜晶体的形式存在,密度为1.1607克/厘米³,熔点在232~236℃(分解)。它可溶于水而不溶于醚等有机溶剂。甘氨酸具有甜味,在水中被茚三酮氧化生成甲醛,并能在强酸或强碱中溶解,表现出两性特征,能被酒精沉淀析出。其合成通常通过α-卤代酸与浓氨水作用完成。

甘氨酸在动物体内参与多种重要化合物的合成,如可与氨、甲酸和二氧化碳结合生成嘌呤类物质;并与琥珀酸合成卟啉类物质。它还是肌酸、甘氨胆酸和谷胱甘肽等化合物的合成原料之一,在人体内起到解毒作用。例如,甘氨酸可以与芳香类物质结合形成无毒物,并通过肝脏氧化后排出体外。此外,甘氨酸还用作氨基酸农药,如每1万平方米(约15亩)甘蔗田喷洒85%的甘氨酸溶液2.5公斤,可增加甘蔗糖分12.9%;N-磷酸甲酯甘氨酸作为一种有效的除草剂,每1万平方米使用1.5公斤即可消灭杂草。近年来,甘氨酸还用于制造抗癌药物,具有显著疗效。

目前,甘氨酸已经实现大规模生产,并在多种领域发挥重要作用。

中文名称 英文名称 CAS号 化学式 结构式图片
—— monopotassium 4-hydroxy-α-[(3-methoxy-1-methyl-3-oxo-1-propenyl)amino]benzeneacetate 69416-61-1 C13H14NO5*K
monopotassium 4-hydroxy-α-[(3-methoxy-1-methyl-3-oxo-1-propenyl)amino]benzeneacetate
—— tetramethylammonium glycinate 55378-67-1 C2H4NO2*C4H12N
tetramethylammonium glycinate
—— [(2,3-difluorobenzoyl)amino]acetic acid 1072833-89-6 C9H7F2NO3
[(2,3-difluorobenzoyl)amino]acetic acid
—— cyclohexylglycine methyl ester hydrochloride 322392-74-5 C9H17NO2*ClH
cyclohexylglycine methyl ester hydrochloride
—— glycoβ-muricholic acid 66225-78-3 C26H43NO6
glycoβ-muricholic acid
—— (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose 64003-53-8 C37H61N2O29
(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose
—— methyl N-benzyloxycarbonyl-L-leucylglicynate 5084-98-0 C17H24N2O5
methyl N-benzyloxycarbonyl-L-leucylglicynate
—— N‑[3‑(2‑furyl)acryloyl]-L-phenylalanylglycylglycine 64967-39-1 C20H21N3O6
N‑[3‑(2‑furyl)acryloyl]-L-phenylalanylglycylglycine
—— (2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-acetic acid 16257-05-9 C13H24N2O5
(2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-acetic acid
—— Methyl 2-(dimethoxyphosphinyl)-2-<N-(methoxycarbonyl)amino>ethanoate 144001-86-5 C7H14NO7P
Methyl 2-(dimethoxyphosphinyl)-2-<N-(methoxycarbonyl)amino>ethanoate
—— 2-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid 53994-85-7 C13H16ClNO4
2-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid
—— [Cys-Gly]2 7729-20-6 C10H18N4O6S2
[Cys-Gly]2
—— Pro-Leu-Gly hydroxamate hydrochloride 120928-08-7 C13H25ClN4O4
Pro-Leu-Gly hydroxamate hydrochloride
—— N-(methoxycarbonylmethyl)-N-phenylglycine methyl ester 93136-36-8 C12H15NO4
N-(methoxycarbonylmethyl)-N-phenylglycine methyl ester
—— methyl 2-[((1,1-dimethylethoxy)carbonyl)amino]-4-pentynoate 71460-02-1 C11H17NO4
methyl 2-[((1,1-dimethylethoxy)carbonyl)amino]-4-pentynoate
—— Sodium (Z)-N-methyl-N-(1-oxo-9-octadecenyl)aminoacetate 14351-62-3 C21H38NNaO3
Sodium (Z)-N-methyl-N-(1-oxo-9-octadecenyl)aminoacetate
—— potassium 2-[[(Z)-3-ethoxy-1-methyl-3-oxo-prop-1-enyl]amino]-2-phenyl-acetate 961-69-3 C14H16KNO4
potassium 2-[[(Z)-3-ethoxy-1-methyl-3-oxo-prop-1-enyl]amino]-2-phenyl-acetate
—— 2-[2-[[3-(4-Hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoylamino]acetic acid 64410-47-5 C19H27N3O7
2-[2-[[3-(4-Hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoylamino]acetic acid
—— (2R)-2-amino-4-methyl-N-[2-(naphthalen-2-ylamino)-2-oxoethyl]pentanamide 100930-00-5 C18H23N3O2
(2R)-2-amino-4-methyl-N-[2-(naphthalen-2-ylamino)-2-oxoethyl]pentanamide
—— 2-[[(2R)-5-amino-5-oxo-2-(phenylmethoxycarbonylamino)pentanoyl]amino]acetic acid 6610-42-0 C15H19N3O6
2-[[(2R)-5-amino-5-oxo-2-(phenylmethoxycarbonylamino)pentanoyl]amino]acetic acid
—— Glycine, N,N-bis2-bis(carboxymethyl)aminoethyl-, pentapotassium salt 7216-95-7 C14H23KN3O10
Glycine, N,N-bis2-bis(carboxymethyl)aminoethyl-, pentapotassium salt
—— Gly-pro 4-methoxy-b-naphthylamide*hydroc hloride 100929-90-6 C18H22ClN3O3
Gly-pro 4-methoxy-b-naphthylamide*hydroc hloride
—— [N-[1-[2-(2-Pyridylcarboxamido)phenyl]ethylidene]-glycinato]nickel 264921-97-3 C16H14N3NiO3-
[N-[1-[2-(2-Pyridylcarboxamido)phenyl]ethylidene]-glycinato]nickel
—— 4-Methyl-phenylsulfonylaminoessigsaeure-butylester 92198-71-5 C13H19NO4S
4-Methyl-phenylsulfonylaminoessigsaeure-butylester
—— 2-(~2~H_2_)Amino(~2~H_2_)ethan(~2~H_2_)imidic acid 4896-77-9 C2H6N2O
2-(~2~H_2_)Amino(~2~H_2_)ethan(~2~H_2_)imidic acid
—— Sodium (cyclohexa-1,4-dien-1-yl)[(4-methoxy-4-oxobut-2-en-2-yl)amino]acetate 26774-89-0 C13H16NNaO4
Sodium (cyclohexa-1,4-dien-1-yl)[(4-methoxy-4-oxobut-2-en-2-yl)amino]acetate
—— 2-Hydroxy-N-methyl-2-(methylimino)ethan-1-aminium 44565-47-1 C4H11N2O+
2-Hydroxy-N-methyl-2-(methylimino)ethan-1-aminium
—— (R)-2-(1H-indol-3-yl)glycine 6747-15-5 C10H10N2O2
(R)-2-(1H-indol-3-yl)glycine
—— 2-{[tert-Butoxy(hydroxy)methylidene]amino}pent-4-enoate 170899-08-8 C10H16NO4-
2-{[tert-Butoxy(hydroxy)methylidene]amino}pent-4-enoate
—— (2-nitrophenyl)sulfonyl N,N-diethylcarbamodithioate 42288-20-0 C11H14N2O4S3
(2-nitrophenyl)sulfonyl N,N-diethylcarbamodithioate
—— leucyl-glycine-β-naphthylamide 100930-00-5 C18H23N3O2
leucyl-glycine-β-naphthylamide
—— 2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid 158979-29-4 C10H15NO4
2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid
—— H-Lys-Gly-OH.HCl 40719-58-2 C8H18ClN3O3
H-Lys-Gly-OH.HCl
—— Z-Pro-Leu-Gly-OEt 7784-82-9 C23H33N3O6
Z-Pro-Leu-Gly-OEt
—— N-Phenylglycime sodium salt 10265-69-7 C8H8NO2*Na
N-Phenylglycime sodium salt
—— (2S,3S,4R)-α-(carboxycyclopropyl)glycine 117857-95-1 C6H9NO4
(2S,3S,4R)-α-(carboxycyclopropyl)glycine
—— <i>N</i>-(<i>N</i>-benzyloxycarbonyl-L-seryl)-glycine ethyl ester 4526-93-6 C15H20N2O6
<i>N</i>-(<i>N</i>-benzyloxycarbonyl-L-seryl)-glycine ethyl ester
—— L-lysylglycine hydrochloride 40719-58-2 C8H17N3O3*ClH
L-lysylglycine hydrochloride
—— Diazanium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;iron(3+);hydroxide 68413-60-5 C10H13FeN2O9.2H4N
Diazanium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;iron(3+);hydroxide
—— [copper(II)(diethylene triamine pentaacetate)](3-) 11065-66-0 C14H18N3O10*Cu
[copper(II)(diethylene triamine pentaacetate)](3-)
—— rac-N,N'-Ethylenebis<2-(o-hydroxyphenyl)glycine> 1170-02-1 C18H20N2O6
rac-N,N'-Ethylenebis<2-(o-hydroxyphenyl)glycine>
—— 2-(3-hydroxy-1-adamantyl)-(2S)-aminoethanoic acid 709031-29-8 C12H19NO3
2-(3-hydroxy-1-adamantyl)-(2S)-aminoethanoic acid
—— sivelestat sodium 150374-95-1 C20H21N2O7S*Na
sivelestat sodium
—— potassium D-α-(1-carbomethoxypropen-2-yl)-amino-p-hydroxyphenylacetate 69416-61-1 C13H14NO5*K
potassium D-α-(1-carbomethoxypropen-2-yl)-amino-p-hydroxyphenylacetate
—— N,N-dimethylglycine sodium salt 18319-88-5 C4H8NO2*Na
N,N-dimethylglycine sodium salt
—— N-benzyloxycarbonyl-L-phenylalanylglycylglycine 37700-64-4 C21H23N3O6
N-benzyloxycarbonyl-L-phenylalanylglycylglycine
—— N-(methoxy-carbonyl)-glycine methyl ester 70288-73-2 C5H9NO4
N-(methoxy-carbonyl)-glycine methyl ester
—— N-dithiocarbobenzoxyglycine 4596-57-0 C10H11NO2S2
N-dithiocarbobenzoxyglycine
—— N-Boc-3'-hydroxyadamantylglycine 709031-31-2 C17H27NO5
N-Boc-3'-hydroxyadamantylglycine
—— <i>N</i>-(<i>N</i>-benzyloxycarbonyl-L-valyl)-glycine 22221-75-6 C15H20N2O5
<i>N</i>-(<i>N</i>-benzyloxycarbonyl-L-valyl)-glycine