556-50-3

Basic information

• Product Name: Glycylglycine
• Synonyms: (2-Amino-acetylamino)-aceticacid;[(Aminoacetyl)amino]acetic acid;2-(Aminoacetamido)aceticacid;n-glycyl-glycin;N-GLYCYLGLYCINE;DIGLYCINE;GLYCYLGLYCINE;GLY-GLY-OH
• CAS NO: 556-50-3
• Molecular Formula: C₄H₈N₂O₃
• Molecular Weight: 132.12
• EINECS: 209-127-8
• Product Categories: Biochemistry;Oligopeptides;Peptide Synthesis;Peptide;amino acid;buffer
• Mol File: 556-50-3.mol
• Article Data: 115

Chemical Properties

• Melting Point: 220-240 °C (dec.)
• Boiling Point: 267.18°C (rough estimate)
• Flash Point: 227.9 °C
• Appearance: White/Solid
• Density: 1.5851 (rough estimate)
• Vapor Pressure: 0.058Pa at 20-50℃
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: -15°C
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 3.139(at 25℃)
• Water Solubility: SOLUBLE IN HOT WATER
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,4503
• BRN: 1765223
• CAS DataBase Reference: Glycylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: Glycylglycine(556-50-3)
• EPA Substance Registry System: Glycylglycine(556-50-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 24/25-26
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 556-50-3(Hazardous Substances Data)

Usage

Chemical Properties

White crystals

Uses

Glycylglycine is as a buffering reagent and also used in biochemical research. It is the simplest of all dipeptides and is used as a starting template for preparation of more complex peptides. It is also employed as a practical buffer with a buffering range of 7.5 - 8.9 (at 25°C). Valuable agent for experiments investigating peptide transport and absorption.

Definition

ChEBI: A dipeptide formed from glycine residues.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 5323, 1953 DOI: 10.1021/ja01117a053

Biochem/physiol Actions

Glycine is a non-essential amino acid. Influx of calcium through the cell membrane is mediated by glycine-gated channel. Glycine participates in the synthesis of porphyrins, purine and serine. It also serves as a competitive agonist for glutamate in binding to the NMDA (N-methyl-D-aspartate) receptors. Glycine synthesis might be increased in rapidly proliferating cancer cells, due to increased demand for the amino acid. Diglycine is known to catalyze the formation of homo- and hetero dipeptides more efficiently than glycine.

Purification Methods

Crystallise glycylglycine from aqueous 50% EtOH or water at 50-60o by addition of EtOH. Dry it at 110o. It sublimes at 190-200o/0.3mm with 30% recovery [Gross & Gradsky J Am Chem Soc 77 1678 1955, King J Am Chem Soc 79 6153 1957]. [Beilstein 4 IV 2459.]

InChI:InChI=1/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9)

Synthetic route

glycine (56-40-6) → glycylglycine (556-50-3)

Conditions	Yield
With silica gel In toluene for 20h; Heating;	92.4%
With zeolite Na-BETA In water at 120℃; var. silicates and pH;
Multistep reaction;
With Sodium trimetaphosphate In aq. buffer at 37℃; under 225023 Torr; pH=10.7; Pressure; Temperature;

Boc-Gly-Gly-OH (31972-52-8) → glycylglycine (556-50-3)

Conditions	Yield
With trifluoroacetic acid In dichloromethane Large scale;	84.9%
With trifluoroacetic acid In dichloromethane at -5℃;

Gly-Gly-MCA (208645-74-3) → glycylglycine (556-50-3)

Conditions	Yield
With ethylenediaminetetraacetic acid; dipeptydyl-peptidase DPP5; sodium phosphate; sodium chloride In water at 37℃; for 0.5h; pH=7.0; Catalytic behavior; Enzymatic reaction;

tetrabutylphosphonium glycinate + glycine ethyl ester hydrochloride (5680-79-5) → glycylglycine (556-50-3)

Conditions	Yield
Stage #1: tetrabutylphosphonium glycinate; glycine ethyl ester hydrochloride at 60℃; for 3h; Inert atmosphere; Stage #2: With acetic acid In chloroform at 20℃; for 3h;	54%

glycylglycine ethyl ester (627-74-7) → glycylglycine (556-50-3)

Conditions	Yield
With 15K(1+)*H(1+)*25H2O*O122P4W34Zr(16-); water; hydrogen chloride In water-d2 at 60℃; pH=5;

glycylglycinamide (20238-94-2) → glycylglycine (556-50-3)

Conditions	Yield
With 15K(1+)*H(1+)*25H2O*O122P4W34Zr(16-); water; hydrogen chloride In water-d2 at 60℃; pH=5;

CbzGlyGly (2566-19-0) → glycylglycine (556-50-3)

Conditions	Yield
With trifluoroacetic acid
With nitromethane; hydrogen bromide
With phosphonium iodide; acetic acid at 45 - 50℃; im Wasserstoff-Strom;

N-tritylglycylglycine (5893-07-2) → glycylglycine (556-50-3)

Conditions	Yield
With acetic acid
With ethanol; palladium Hydrogenation;

N--glycine → glycylglycine (556-50-3)

Conditions	Yield
With ethanol; hydrazine hydrate

N-carbamoyl-L-alanine (18409-49-9) + glycine (56-40-6) → L-alanin (56-41-7) + alanylglycine (687-69-4) + glycylglycine (556-50-3) + N-carbamoylglycine (462-60-2)

Conditions	Yield
In phosphate buffer at 80℃; for 1272h; pH=6.8;

glycine-glycine-glycine (556-33-2) → glycylglycine (556-50-3) + glycine (56-40-6)

Conditions	Yield
With (Et2NH2)8[{α-PW11O39Zr-(μ-OH)(H2O)}2]*7H2O; water; 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt In water-d2 at 50℃; for 24h; Reagent/catalyst;

glycyl-glycyl-L-histidine (7451-76-5) → glycylglycine (556-50-3) + L-histidine (71-00-1)

Conditions	Yield
With (Et2NH2)8[{α-PW11O39Zr-(μ-OH)(H2O)}2]*7H2O; water; 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt In water-d2 at 60℃; Reagent/catalyst;

chloroacetyldiglycine (15474-96-1) → glycylglycine (556-50-3)

Conditions	Yield
With lithium hydroxide; water; 1,2-diamino-benzene

N-(N-benzyloxycarbonyl-glycyl)-glycine-(4-nitro-benzyl ester) (3916-37-8) → glycylglycine (556-50-3)

Conditions	Yield
With hydrogenchloride; methanol; palladium on activated charcoal Hydrogenation.R 4:THF;

N-{N-[(2-nitro-phenoxy)-acetyl]-glycyl}-glycine (39522-14-0) → glycylglycine (556-50-3)

Conditions	Yield
With sodium hydrogencarbonate; platinum Hydrogenation.Erhitzen des Reaktionsprodukts mit H2O;

[2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-acetylamino]-acetic acid (78641-72-2) → glycylglycine (556-50-3) + 3,5-Dinitro-1-propyl-1H-pyridin-4-one (78641-61-9)

Conditions	Yield
With propylamine	A 80% B n/a

Glycine anhydride (106-57-0) → glycylglycine (556-50-3)

Conditions	Yield
With lithium hydroxide
With ammonia; water
With lithium hydroxide

phenyl isothiocyanate (103-72-0) + Ac-Ala-DAPA-Gly-Gly-OH (121574-49-0) → glycylglycine (556-50-3) + (S)-2-Acetylamino-N-((S)-6-oxo-2-phenylamino-5,6-dihydro-4H-[1,3]thiazin-5-yl)-propionamide

Conditions	Yield
With N-ethylmorpholine;; acetic acid In ethanol at 37℃; for 2.5h; Product distribution; other reagents, other times, other temp.;

H2N-GGSEFG-COOH (1419234-19-7) + H2N-Y-ALPETGG-COOH → glycylglycine (556-50-3) + H2N-YALPETGGSEFG-COOH (1419234-20-0)

Conditions	Yield
With sortase A; sodium chloride; calcium chloride In aq. buffer at 37℃; pH=7.5; Enzymatic reaction;

glycine (56-40-6) → Glycine anhydride (106-57-0) + glycylglycine (556-50-3)

Conditions	Yield
With silica gel In toluene for 20h; Heating;	A 44.3% B 10.7%
With silica gel In toluene for 20h; Product distribution; Heating; glycine adsorbed on silica gel;
In water at 200℃; under 187515 Torr; pH=6.1; Kinetics; Equilibrium constant; Further Variations:; Temperatures;
With 2Zn(2+)*2H2O*C8MoN8(4-) at 120℃; for 840h; Reagent/catalyst; Temperature;	A 20.3 %Chromat. B 19.23 %Chromat.

glycine (56-40-6) → sarcosine (107-97-1) + N-methylglycine methylester (5473-12-1) + glycylglycine (556-50-3) + iminodiacetic acid (142-73-4)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 180℃; under 300.03 Torr; for 0.166667h;

N-chloroglycylglycine (53090-33-8) → glycylglycine (556-50-3)

Conditions	Yield
With sulfite(2-) In various solvent(s) at 25℃; pH=8.59; Kinetics; Dehalogenation; UV-irradiation;

N-(N-carboxy-glycyl)-glycine (27440-15-9) → glycylglycine (556-50-3)

Conditions	Yield
With borax; sodium dihydrogenphosphate at 26℃; Equilibrium constant;

2-<1-(2,5-dimethylpyrrolyl)>acetylglycine → glycylglycine (556-50-3)

Conditions	Yield
With potassium hydroxide; hydroxylamine hydrochloride In methanol; water for 24h; Heating; Yield given;

glycine (56-40-6) → Glycine anhydride (106-57-0) + glycine-glycine-glycine (556-33-2) + tetraglycine (637-84-3) + glycylglycine (556-50-3)

Conditions	Yield
With hydrogen In water at 200℃; under 187515 Torr; for 0.0333333h; Product distribution; Further Variations:; Temperatures; Reagents;

(CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH2COO)) → (R(c),R,S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene + glycylglycine (556-50-3)

Conditions	Yield
With hydrogenchloride; sodium carbonate In water acid hydrolysis by addn. of 3N HCl, then neutralized by Na2CO3, extd. with CCl4;

(CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH2COO)) → (R,S(c),R,S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene + glycylglycine (556-50-3)

Conditions	Yield
With hydrogenchloride; sodium carbonate In water acid hydrolysis by addn. of 3N HCl, then neutralized by Na2CO3, extd. with CCl4;

N-(chloroacetyl)glycine (6319-96-6) → glycylglycine (556-50-3)

Conditions	Yield
With ammonia; water

Cbz-Gly-Gly-OBn (19525-53-2) → glycylglycine (556-50-3)

Conditions	Yield
With hydrogen bromide; acetic acid

N-(N-benzylsulfanylcarbonyl-glycyl)-glycine (100135-84-0) → glycylglycine (556-50-3)

Conditions	Yield
With 1,4-dioxane; Perbenzoic acid; water
With Perbenzoic acid; water; benzene
With Perbenzoic acid; water; acetic acid

glycylglycine (556-50-3) → Glycine anhydride (106-57-0)

Conditions	Yield
With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h; Solvent; Reagent/catalyst;	100%
With silica gel In gas at 180 - 200℃; under 0.08 Torr;	46%
With hydrogenchloride at 150 - 160℃; im Rohr;

glycylglycine (556-50-3) + N,N-diethyl-1,1,1-trimethylsilanamine (996-50-9) → N,O-bis(trimethylsilyl)glycyl-glycine (39553-15-6)

Conditions	Yield
In acetonitrile for 2h;	100%

glycylglycine (556-50-3) + toluene-4-sulfonic acid (104-15-4) + allyl alcohol (107-18-6) → PTSA*H-Gly-Gly-OAll (1188307-54-1)

Conditions	Yield
In toluene Reflux; Inert atmosphere;	100%

glycylglycine (556-50-3) + (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (769922-77-2) → (5S)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid (37700-64-4)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃;	98%

sodium tetrachloropalladate(II) + glycylglycine (556-50-3) → Dichlorobis(diglycinato)palladium(II) (89954-58-5)

Conditions	Yield
In water stirring for etwa 13h; filtration, washing twofold with water, drying in vac., elem.anal.;	98%

glycylglycine (556-50-3) + N,3-diphenyl-N-((trifluoromethyl)sulfonyl)propiolamide → phenyl trifluoromethanesulfonamide (456-64-4) + (3-phenylpropioloyl)glycylglycine

Conditions	Yield
In methanol; water at 20℃; for 5h; Green chemistry; chemoselective reaction;	A n/a B 97%

glycylglycine (556-50-3) + C52H39N5O7 → C52H42N6O7

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 40℃;	93%

indole (120-72-9) + formaldehyd (50-00-0) + glycylglycine (556-50-3) → N,N-bis[(1H-indol-3-yl)methyl]glycylglycine

Conditions	Yield
Stage #1: formaldehyd; glycylglycine In water at 55℃; Mannich Aminomethylation; Stage #2: indole In ethanol; water at 55℃; for 0.5h; Mannich Aminomethylation;	93%

glycylglycine (556-50-3) + benzoyl chloride (98-88-4) → N-(N'-benzoyl-2-aminoethanoyl)-2-aminoethanoic acid (1145-32-0)

Conditions	Yield
With dodecyltrimethylammonium bromide; sodium carbonate In tetrahydrofuran Heating;	92%

dibutyl hydrogen phosphite (1809-19-4) + glycylglycine (556-50-3) → N-(O,O-dibutylphosphoryl)-glycyl-glycine (136884-29-2)

Conditions	Yield
With triethylamine In tetrachloromethane; ethanol; water 1) -3 - 0 deg C, 7-8 h, 2) r.t., 5-6 h;	92%

glycylglycine (556-50-3) + N2-tetrabromophthaloyl-L-aspartic anhydride (138202-17-2) → {2-[(S)-2,5-Dioxo-3-(4,5,6,7-tetrabromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidin-1-yl]-acetylamino}-acetic acid (138202-30-9)

Conditions	Yield
In acetic acid 1.) 20 deg C, 30 min, 2.) 120 deg C;	92%

glycylglycine (556-50-3) + [2-Oxo-2-(2-thioxo-thiazolidin-3-yl)-ethyl]-carbamic acid benzyl ester (80681-01-2) → [2-(2-Benzyloxycarbonylamino-acetylamino)-acetylamino]-acetic acid (2566-20-3)

Conditions	Yield
Ambient temperature;	90%

glycylglycine (556-50-3) + N-succinimidyl 3-[3,3-dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b][1,4]oxazine)]-1-yl]-propionate (256235-92-4) → 3-[3,3-dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b][1,4]oxazine)]-1-yl]propionylglycylglycine (256235-93-5)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 6h;	90%

glycylglycine (556-50-3) + 7-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-ethyl-[1,3]dioxolo[4,5-g]quinolin-8(5H)-one (1131147-59-5) → 2-[2-(5-ethyl-8-oxo-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxamido)acetamido]-3-acetic acid (1131147-69-7)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 3h;	90%

glycylglycine (556-50-3) + 1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole (1131148-55-4) → 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid (35665-38-4)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 2h;	90%

glycylglycine (556-50-3) + allyl 1H-benzo[d][1,2,3]triazole-1-carboxylate (114416-17-0) → 2-[2-{({allyloxy}carbonyl)amino}acetamido]acetic acid (343260-53-7)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 2h;	90%

glycylglycine (556-50-3) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid (35665-38-4)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 12h;	89%
With sodium carbonate In 1,4-dioxane; water at 20℃;	77%

glycylglycine (556-50-3) + copper diacetate (142-71-2) + o-hydroxyacetophenone (118-93-4) + potassium hydroxide → K[Cu(N-2-hydroxyacetophenoneglycylglycine-3H)]*2.5H2O

Conditions	Yield
In ethanol; water N compd. dissolved in aq. EtOH (1:2) containing KOH, cooled to room temp., soln. of aromatic compd. in abs. EtOH added slowly with stirring for 1.5 h, aq. soln. of Cu compd. added dropwise, pH adjusted with KOH to 9-10, stirred at 50°C for 8 h; filtered, concd., pptd. with acetone, recrystd. from water/acetone, dried in vac. over P2O5 at 35°C; elem. anal.;	89%

glycylglycine (556-50-3) + 4-methyl-1,2,3-thiadiazol-5-ylcarbonylazide → N-{[(4-methyl-1,2,3-thiadiazol-5-yl)carbamoyl]aminoacetyl}aminoacetic acid

Conditions	Yield
In 1,4-dioxane for 3h; Reflux;	89%

glycylglycine (556-50-3) + N-phthaloylglycine chloride (6780-38-7) → N-[N-(N,N-phthaloyl-glycyl)-glycyl]-glycine (93923-88-7)

Conditions	Yield
Stage #1: glycylglycine With magnesium oxide In water at 25℃; for 4h; Stage #2: N-phthaloylglycine chloride In 1,4-dioxane; water at 25℃; for 2h;	87%
With 1,4-dioxane; sodium acetate; acetic acid
With water; sodium hydrogencarbonate; benzene

Upstream product

• 107-15-3 Ethylenediamine 

Downstream Products

• 55650-58-3 (S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE 
• 55650-59-4 (S)-N,N-DIMETHYL-1-[(R)-1',2-BIS(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE 
• 5565-07-1 4-fluoro-N-[4-(1,3-thiazol-2-ylsulfamoyl)phenyl]benzamide 
• 5565-08-2 (5Z)-3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-5-(naphthalen-1-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one 
• 5565-09-3 (3R,5R)-3-(dimethylamino)-5-methyl-1-phenylpyrrolidin-2-one hydrochloride (1:1) 
• 5565-10-6 (3S,5R)-3-(dimethylamino)-5-methyl-1-phenylpyrrolidin-2-one hydrochloride (1:1) 
• 55651-28-0 16-bromo-11-methylgona-1(10),2,4,6,8,11,13-heptaen-17-one 
• 55651-29-1 11-methylgona-1(10),2,4,6,8,11,13,15-octaen-17-one 
• 55651-30-4 11-methyl-17-oxogona-1(10),2,4,6,8,11,13-heptaen-15-yl acetate 
• 55651-31-5 15-hydroxy-11-methylgona-1(10),2,4,6,8,11,13-heptaen-17-one 
• 55651-35-9 [17-oxogona-1(10),2,4,6,8,11,13-heptaen-11-yl]methyl acetate 
• 55651-36-0 11-(Hydroxymethyl)-15,16-dihydro-17H-cyclopenta[a]phenanthrene-17-one 
• 5565-14-0 2H-Pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione,tetrahydro-(7CI,8CI,9CI) 
• 55651-42-8 2-methoxygona-1,3,5(10),6,8,13-hexaen-17-one 

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