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Merck

15420

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:
Molecular Weight:
175.18
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
224-864-5
MDL number:
Beilstein/REAXYS Number:
1101514

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Product Name

Boc-Gly-OH, ≥99.0% (T)

InChI key

VRPJIFMKZZEXLR-UHFFFAOYSA-N

InChI

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

SMILES string

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

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

Quality Level

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1 of 4

This Item
1542315456359688
form

powder or crystals

form

solid

form

solid

form

solid

assay

≥99.0% (T)

assay

≥99.0% (T)

assay

≥99.0% (NT)

assay

99%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

mp

86-89 °C (lit.)

mp

165-167 °C

mp

~205 °C (dec.) (lit.)

mp

~205 °C (dec.) (lit.)

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

ign. residue

≤0.05%

ign. residue

≤0.05%

ign. residue

-

ign. residue

-

Application

Boc-Gly-OH can be used:
  • For the esterification reaction to synthesize N-Boc amino acid esters for peptide chemistry.[1]
  • For the synthesis of tripeptide H-Gly-Pro-Glu-OH, analogs of neuroprotective drugs.[2]
  • As a promoter for the allylation of hydrazones and isatin.[3]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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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)
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)
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)
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

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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