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858919

Sigma-Aldrich

D-Proline

≥99%, for peptide synthesis, ReagentPlus®

Sinonimo/i:

(R)-Pyrrolidine-2-carboxylic acid

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500 MG
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5 G
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About This Item

Formula empirica (notazione di Hill):
C5H9NO2
Numero CAS:
344-25-2
Peso molecolare:
115.13
Beilstein:
80811
Numero CE:
206-452-7
Numero MDL:
MFCD00064317
Codice UNSPSC:
12352209
ID PubChem:
24888479
NACRES:
NA.22

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Nome del prodotto

D-Proline, ReagentPlus®, ≥99%

Livello qualitativo

200

Nome Commerciale

ReagentPlus®

Saggio

≥99%

Stato

powder

Attività ottica

[α]22/D +85.0°, c = 4 in H2O

Purezza ottica

ee: 98% (GLC)

Impiego in reazioni chimiche

reaction type: solution phase peptide synthesis

Punto di fusione

223 °C (dec.) (lit.)

applicazioni

peptide synthesis

Stringa SMILE

OC(=O)[C@H]1CCCN1

InChI

1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
ONIBWKKTOPOVIA-SCSAIBSYSA-N

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Applicazioni

D-Proline is a key starting material in the total synthesis of (−)-secu′amamine A[1] and (R)-harmicine.[2]
  • It can be used as a ligand for the synthesis of chiral polyoxometalate (POM) clusters.[3]
  • It can also be used as a catalyst in the enantioselective α-aminoxylation of aldehydes.[4]

Note legali

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
STBK9046
STBK8446
STBC4290V
1448244
1451623

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Sigma-Aldrich

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L-prolina Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1332

L-prolina

Synthesis of (S)?and (R)?Harmicine from Proline: An Approach Toward Tetrahydro?β?carbolines.
Lood C S and Koskinen A M
European Journal of Organic Chemistry, 2014(11), 2357-2364 (2014)
Michael Meanwell et al.
Science (New York, N.Y.), 369(6504), 725-730 (2020-08-09)
Nucleoside analogs are commonly used in the treatment of cancer and viral infections. Their syntheses benefit from decades of research but are often protracted, unamenable to diversification, and reliant on a limited pool of chiral carbohydrate starting materials. We present
A Facile and Rapid Route to Highly Enantiopure 1, 2?Diols by Novel Catalytic Asymmetric α?Aminoxylation of Aldehydes.
Zhong G
Angewandte Chemie (International Edition in English), 115(35), 4379-4382 (2003)
Chiral 3D architectures with helical channels constructed from polyoxometalate clusters and copper?amino acid complexes.
An H Y, et al.
Angewandte Chemie (International Edition in English), 118(6), 918-922 (2006)
Total Synthesis of the Securinega Alkaloid (−)-Secu?amamine A.
Liu P, et al.
Journal of the American Chemical Society, 130(24), 7562-7563 (2008)
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Questions

1–2 of 2 Questions  

  1. 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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  2. 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/449/386/product-dating-information-mk.pdf

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