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15420

Sigma-Aldrich

Boc-Gly-OH

≥99.0% (T), for peptide synthesis

Synonym(s):

N-(tert-Butoxycarbonyl)glycine, Boc-glycine

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About This Item

Linear Formula:
(CH3)3COCONHCH2COOH
CAS Number:
4530-20-5
Molecular Weight:
175.18
Beilstein:
1101514
EC Number:
224-864-5
MDL number:
MFCD00002690
UNSPSC Code:
12352209
PubChem Substance ID:
57647418
NACRES:
NA.22

product name

Boc-Gly-OH, ≥99.0% (T)

Assay

≥99.0% (T)

form

powder or crystals

reaction suitability

reaction type: Boc solid-phase peptide synthesis

ign. residue

≤0.05%

mp

86-89 °C (lit.)
86-89 °C

application(s)

peptide synthesis

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD6914
BCBZ9468
BCBV1582
BCBR2160V
BCBJ8075V

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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)
N-Boc-glycine-assisted indium-mediated allylation reaction: a sustainable approach.
Vemula SR, et al.
Tetrahedron Letters, 56(23), 3322-3325 (2015)
L Varga et al.
Hepato-gastroenterology, 27(2), 146-149 (1980-04-01)
The catabolism of the 14C-labelled pentagastrin was investigated in rats. The following results were found: -- the labelled BOC-glycine fragment is split off the pentagastrin in the small intestine -- it is absorbed through the intestinal wall, and -- enters
Klaus Schmidt-Rohr et al.
Journal of the American Chemical Society, 125(19), 5648-5649 (2003-05-08)
A new magic-angle spinning NMR method for measuring internuclear distances between a 13C-labeled site and amide protons is described. The magnetization of the protons evolves under homonuclear decoupling and the recoupled 13C-1H dipolar interaction, which provides simple spin-pair REDOR curves
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