15420

Sigma-Aldrich

Boc-Gly-OH

≥99.0% (T)

Synonym(s):
N-(tert-Butoxycarbonyl)glycine, Boc-glycine
Linear Formula:
(CH3)3COCONHCH2COOH
CAS Number:
Molecular Weight:
175.18
Beilstein/REAXYS Number:
1101514
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99.0% (T)

reaction suitability

reaction type: Boc solid-phase peptide synthesis

application(s)

peptide synthesis: suitable

ign. residue

≤0.05%

mp

86-89 °C (lit.)
86-89 °C

SMILES string

CC(C)(C)OC(=O)NCC(O)=O

InChI

1S/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)

InChI key

VRPJIFMKZZEXLR-UHFFFAOYSA-N

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Application

Boc-Gly-OH can be used:
  • For the esterification reaction to synthesize N-Boc amino acid esters for peptide chemistry.
  • For the synthesis of tripeptide H-Gly-Pro-Glu-OH, analogs of neuroprotective drugs.
  • As a promoter for the allylation of hydrazones and isatin.

Packaging

5, 25, 100 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Ceric ammonium nitrate (CAN) mediated esterification of N-Boc amino acids allows either retention or removal of the N-Boc group.
Kuttan A, et al.
Tetrahedron Letters, 45(12), 2663-2665 (2004)
Analogues of the neuroprotective tripeptide Gly-Pro-Glu (GPE): synthesis and structure-activity relationships.
De Diego SAA, et al.
Bioorganic & Medicinal Chemistry Letters, 15(9), 2279-2283 (2005)
Wen-Ren Li et al.
The Journal of organic chemistry, 67(14), 4702-4706 (2002-07-06)
A new approach to a CD45 protein tyrosine phosphatase inhibitor, pulchellalactam, is described. The key step of the sequence involves addition and elimination of an enolic lactam in a single step and 70% yield, employing an organocuprate reagent. The resulting...
Alexey Krushelnitsky et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 182(2), 339-342 (2006-07-21)
As demonstrated by means of the one-dimensional solid-state MAS exchange experiment (CODEX), the rate of the proton driven spin diffusion between backbone (15)N nuclei in totally enriched protein depends strongly on the magic angle spinning (MAS) frequency: spin diffusion at...
N-Boc-glycine-assisted indium-mediated allylation reaction: a sustainable approach.
Vemula SR, et al.
Tetrahedron Letters, 56(23), 3322-3325 (2015)
Articles
With a growing peptide drug market the fast, reliable and uncomplicated synthesis of peptides is of paramount importance.
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