(2-Azidoacetyl)glycylglycine

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(2-Azidoacetyl)glycylglycine Basic information
Product Name:(2-Azidoacetyl)glycylglycine
Synonyms:N3-Gly-Gly-Gly-OH;N-(2-azidoacetyl)glycylglycine;(2-Azidoacetyl)glycylglycine;Azido triglycine
CAS:1993176-75-2
MF:C6H9N5O4
MW:215.17
EINECS:
Product Categories:
Mol File:1993176-75-2.mol
(2-Azidoacetyl)glycylglycine Structure
(2-Azidoacetyl)glycylglycine Chemical Properties
form crystalline powder
pka3.309±0.10(predicted)
color White
Safety Information
HS Code 2929900090
MSDS Information
(2-Azidoacetyl)glycylglycine Usage And Synthesis
UsesN3-Gly-Gly-Gly-OH is a oligo-Gly click chemistry reagent containing an azide group. Oligo-Gly also has been used as linker to combine different subunits of dimeric or oligomeric proteins or to create artificial multi-domain proteins. By modification into Gly-Gly-Gly-Ser motifs high solubility can be achieved[1][2][3]. N3-Gly-Gly-Gly-OH is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.
References[1] Imanishi M, et al. DNA-bending finger: artificial design of 6-zinc finger peptides with polyglycine linker and induction of DNA bending. Biochemistry. 2000 Apr 18;39(15):4383-90. DOI:10.1021/bi992989b
[2] Tsygankova SV, et al. Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium. Beilstein J Org Chem. 2014 Jun 17;10:1372-82. DOI:10.3762/bjoc.10.140
[3] Hashii N, et al. [Site-specific O-Glycosylation Analysis of Therapeutic Fc-fusion Protein by Mass Spectrometry]. Yakugaku Zasshi. 2018;138(12):1483-1494. Japanese. DOI:10.1248/yakushi.18-00020-2
(2-Azidoacetyl)glycylglycine Preparation Products And Raw materials
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1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester MC-Val-Cit-PAB DBCO-C6-NHS ester Maleimide-DOTA Mal-PEG2-NHS ester DBCO-NHS Ester