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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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