N-alpha-t-Butyloxycarbonyl-beta,beta-dimethyl-L-serine | CAS 102507-13-1

Element: butyloxycarbonyl dimethyl serine alpha beta beta

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Identification

N-alpha-t-Butyloxycarbonyl-beta,beta-dimethyl-L-serine

CAS:

102507-13-1

EINECS:

Molecular Formula:

C₁₀H₁₉NO₅

MDL:

MFCD03094792

Synonym:

(s)-boc-beta-hydroxy-valine ; n-boc-3-hydroxy-l-valine, 97% ; 3-hydroxy-l-valine, n-boc protected ; (s)-2-boc-amino-3-hydroxy-3-methylbutyric acid ; (s)-boc-2-amino-3-hydroxy-3-methyl-butyric acid ; boc-l-ser(3,3-dimethyl) ; boc-(s)-2-amino-3-hydroxy-3-methylbutanoic acid ; boc-s-ser(3,3me2)-oh ; (s)-2-n-boc-amino-3-hydroxy-3-methylbutyric acid ; (s)-boc-beta,beta-dimethyl-serine

Description

beta,beta-Dimethylation of amino acids stabilizes appropriate peptides towards digestion by proteases. The hydroxyl function of this serine building block is unprotected, because acylation does not happen to tertiary alcohols during standard Boc/Bzl coupling protocols. Reference: A General Method for Making Peptide Therapeutics Resistant to Serine Protease Degradation: Application to Dipeptidyl Peptidase IV Substrates; Kathryn R. Heard, Wengen Wu, Youhua Li, Peng Zhao, Iwona Woznica, Jack H. Lai, Martin Beinborn, David G. Sanford, Matthew T. Dimare, Amrita K. Chiluwal, Diane E. Peters, Danielle Whicher, James L. Sudmeier, and William W. Bachovchin; J. Med. Chem. 2013; 56: 8339-8351. dx.doi.org/10.1021/jm400423p. Total synthesis of the large non-ribosomal peptide polytheonamide B; Masayuki Inoue, Naoki Shinohara, Shintaro Tanabe, Tomoaki Takahashi, Ken Okura, Hiroaki Itoh, Yuki Mizoguchi, Maiko Iida, Nayoung Lee and Shigeru Matsuoka; Nature Chem. 2010; 2: 281-285. DOI: 10.1038/nchem.554.

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Prices & Availability

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Properties for N-alpha-t-Butyloxycarbonyl-beta,beta-dimethyl-L-serine

Molecular Weight:

233.26 g·mol−1

Melting point:

116-118 °C

Physical Description:

white powder

Hazard Statements

GHS03
Harmful

Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, categories 2, 3
Eye irritation, category 2A
Skin sensitization, category 1
Specific target organ toxicity following single exposure, category 3
- Respiratory tract irritation
- Narcotic effects

Not used

with the "skull and crossbones" pictogram
for skin or eye irritation if:
the "corrosion" pictogram also appears
the "health hazard" pictogram is used to indicate respiratory sensitization

Safety & Transport Information

Risk Codes:

R36/37/38 - Irritating to eyes, respiratory system and skin

Safety Codes:

S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection

Hazard Classes:

irritant

Alternative Distributors of [N-alpha-t-Butyloxycarbonyl-beta,beta-dimethyl-L-serine]

Producers or manufacturers change the product range from time to time. The following companies
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